Pesticidal compounds

ABSTRACT

The present invention relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein the variables are defined according to the description, formula (I). The compounds of formula (I), as well as the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

CROSS-REFERENCE TO RELATED APPLICATIONS

This is the U.S. national phase of International Application No.PCT/EP2018/084334, filed Dec. 11, 2018, which claims the benefit ofEuropean Patent Application No. 17209208.2, filed on Dec. 21, 2017.

Invertebrate pests and in particular insects, arachnids and nematodesdestroy growing and harvested crops and attack wooden dwelling andcommercial structures, thereby causing large economic loss to the foodsupply and to property. Accordingly, there is an ongoing need for newagents for combating invertebrate pests.

Carbamoylated and thiocarbamoylated oxime derivatives are known forpesticidal use, for example, in patent publication WO 2016/156076,semi-carbazones and thiosemicarbazones derivatives are known forpesticidal use in patent publication WO 2016/116445 and WO2018/177781

Due to the ability of target pests to develop resistance topesticidally-active agents, there is an ongoing need to identify furthercompounds, which are suitable for combating invertebrate pests such asinsects, arachnids and nematodes. Furthermore, there is a need for newcompounds having a high pesticidal activity and showing a broad activityspectrum against a large number of different invertebrate pests,especially against difficult to control insects, arachnids andnematodes.

It is therefore an object of the present invention to identify andprovide compounds, which exhibit a high pesticidal activity and have abroad activity spectrum against invertebrate pests.

It has been found that these objects can be achieved by substitutedbicyclic compounds of formula I, as depicted and defined below,including their stereoisomers, their salts, in particular theiragriculturally or veterinarily acceptable salts, their tautomers andtheir N-oxides.

In a first aspect, the present invention relates to the compounds offormula I,

wherein

-   A¹ is N or CR^(A);-   A² is N or CR^(B);-   A³ is N or CR^(B1);-   W is O, S(═O)_(m), or NR⁶;-   R^(A), R^(B) and R^(B1) independently of each other are H, halogen,    N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,    C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl,    alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or    substituted with halogen,-   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),    O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,    NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d),    SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy, phenylcarbonyl,    phenylthio, or —CH₂-phenyl, wherein the phenyl rings are    unsubstituted or substituted with R^(f);-   Q is —N═C(X)—, —N(R²)—C(═NR)—, or —N(R²)—C(═S)—; wherein Ar is bound    to either side of Q;-   X is identical or different, H, halogen, SR⁷, OR⁸, N(R³)₂,    —CR⁴═N(OCH₃), CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl    moieties are unsubstituted or substituted with halogen;    -   phenyl, or —CH₂-phenyl, wherein the phenyl rings are        unsubstituted or substituted with R⁵;-   R⁵ is halogen, N₃, OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylthio,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkylthio, alkenyl, alkynyl, cycloalkyl,    cycloalkoxy and cycloalkylthio moieties are unsubstituted or    substituted with halogen,    -   C(O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylen-NR^(b)R^(c),        O—C₁-C₆-alkylen-NR^(b)R^(c), C₁-C₆-alkylen-CN,        NH—C₁-C₆-alkylen-NR^(b)R^(c), C(O)—NR^(b)R^(c), C(O)—R^(d),        SO₂NR^(b)R^(c), or S(═O)_(m)R^(e);-   R² is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C(O)—OR^(a), C₁-C₆-alkylen-NR^(b)R^(c), C₁-C₆-alkylen-CN,        C(O)—NR^(b)R^(c), C(O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e),        phenyl, or —CH₂-phenyl, wherein the phenyl rings are        unsubstituted or substituted with R^(f);-   R is identical or different, H, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, wherein the alkyl, alkenyl, alkynyl    and cycloalkyl moieties are unsubstituted or substituted with    halogen,    -   SR⁷, OR⁸, N(R³)₂, phenyl, or —CH₂-phenyl, wherein the phenyl        rings are unsubstituted or substituted with R⁵;-   R⁴ is H, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, or —CH₂-phenyl, wherein        the phenyl rings are unsubstituted or substituted with R^(f);-   R⁷ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, or —CH₂-phenyl, wherein        the phenyl rings are unsubstituted or substituted with R^(f);-   R⁸ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), phenyl, or        —CH₂-phenyl, wherein the phenyl rings are unsubstituted or        substituted with R^(f);-   R³, R⁶ are, identical or different, H, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e),        phenyl, or —CH₂-phenyl, wherein the phenyl rings are        unsubstituted or substituted with R^(f);-   Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or    substituted with R^(Ar), wherein-   R^(Ar) is halogen, N₃, OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,    C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,    alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or    substituted with halogen,    -   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),        O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d),        SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy,        phenylcarbonyl, phenylthio or —CH₂-phenyl, wherein phenyl rings        are unsubstituted or substituted with R^(f);-   R¹ is a moiety of formula Y—Z-T-R¹¹ or Y—Z-T-R¹²; wherein-   Y is —CR^(ya)═N—, wherein the N is bound to Z;-   NR^(yc)—C(═O)—, wherein C(═O) is bound to Z; or-   —NR^(yc)—C(═S)—, wherein C(═S) is bound to Z;-   Z is a single bond;    -   —NR^(zc)—C(═O)—, wherein C(═O) is bound to T;    -   —NR^(zc)—C(═S)—, wherein C(═S) is bound to T;    -   —N═C(S—R^(za))—, wherein T is bound to the carbon atom; or    -   —NR^(zc)—C(S—R^(za))═, wherein T is bound to the carbon atom;    -   T is O, N or N—R^(T);-   R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), aryl, arylcarbonyl,        aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl, hetaryl,        carbonyl-hetaryl, hetaryl-C₁-C₄-alkyl or hetaryloxy-C₁-C₄-alkyl,        wherein the phenyl rings are unsubstituted or substituted with        R^(g) and wherein the hetaryl is a 5- or 6-membered monocyclic        hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl;-   R¹² is a radical of the formula A¹;

-   wherein # indicates the point of attachment to T;-   R¹²¹, R¹²², R¹²³ are, identical or different, H, halogen,    C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,    C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonlyoxy,    C₁-C₆-alkenylcarbonlyoxy, C₃-C₆-cycloalkylcarbonlyoxy, wherein the    alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and    cycloalkyl moieties are unsubstituted or substituted with halogen,    or NR^(b)R^(c), or one of R¹²¹, R¹²², R¹²³ may also be oxo;-   R¹²⁴ is H, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy, or    C₂-C₆-alkenyloxy, wherein the alkyl, alkoxy, alkenyl and alkenyloxy    moieties are unsubstituted or substituted with halogen;-   and where-   R^(ya) is H, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e),        phenyl, or —CH₂-phenyl, wherein the phenyl rings are        unsubstituted or substituted with R^(f);-   R^(yc), R^(zc) are, identical or different, H, C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy,    C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, or    C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl,    alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or    substituted with halogen;-   R^(T) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₄-alkyl-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e),        phenyl, or —CH₂-phenyl, wherein the phenyl rings are        unsubstituted or substituted with R^(f);-   R^(zc) together with R^(T) if present, may form C₁-C₆-alkylene or a    linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene    and the linear C₂-C₆-alkenylene a CH₂ moiety may be replaced by a    carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moieties may be    replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the    linear C₂-C₆-alkenylene may be unsubstituted or substituted with    R^(h);-   R^(za) is H, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,    tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy,    C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy,    C₁-C₄-alkyl-C₃-C₆-cycloalkyl, wherein the alkyl, alkoxy, alkenyl,    alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or    substituted with halogen,    -   C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, phenylcarbonyl, or        —CH₂-phenyl, wherein the phenyl rings are unsubstituted or        substituted with R^(f);-   R^(za) together with R^(T) if present, may form C₁-C₆-alkylene or a    linear C₂-C₆-alkenylene group, where in the linear C₁-C₆-alkylene    and the linear C₂-C₆-alkenylene a CH₂ moiety may be replaced by a    carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moieties may be    replaced by O or S and/or wherein the linear C₁-C₆-alkylene and the    linear C₂-C₆-alkenylene may be unsubstituted or substituted with    R^(h);-   R^(a), R^(b) and R are, identical or different, H, C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,    C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,    alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or    substituted with halogen,    -   C₁-C₆-alkylene-CN, phenyl, or —CH₂-phenyl, wherein the phenyl        rings are unsubstituted or substituted with R^(f);-   R^(d) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein    the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy    moieties are unsubstituted or substituted with halogen,    -   phenyl, or —CH₂-phenyl, wherein the phenyl rings are        unsubstituted or substituted with R^(f);-   R^(e) is C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, wherein the alkyl, cycloalkyl moieties    are unsubstituted or substituted with halogen, phenyl and    —CH₂-phenyl, wherein the phenyl rings are unsubstituted or    substituted with R^(f);-   R^(f) is halogen, N₃, OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,    C₃-C₆-cycloalkoxyx-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,    alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or    substituted with halogen,    -   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),        O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d),        SO₂NR^(b)R^(c), or S(═O)_(m)R^(e);-   R^(g) is halogen, N₃, OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,    C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,    alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or    substituted with halogen,    -   C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),        O—C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN,        NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d),        SO₂NR^(b)R^(c), or S(═O)_(m)R^(e);-   R^(h) is halogen, OH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, or CN;-   m is 0, 1, or 2;-   with a proviso that when Z is a single bond, R^(T) is other than H;    and the N-oxides, stereoisomers, tautomers and agriculturally or    veterinarily acceptable salts thereof.

Moreover, the present invention also relates to processes andintermediates for preparing compounds of formula I and to activecompound combinations comprising them. Moreover, the present inventionrelates to agricultural or veterinary compositions comprising thecompounds of formula I, and to the use of the compounds of formula I orcompositions comprising them for combating or controlling invertebratepests and/or for protecting crops, plants, plant propagation materialand/or growing plants from attack and/or infestation by invertebratepests. The present invention also relates to methods of applying thecompounds of formula I. Furthermore, the present invention relates toseed comprising compounds of formula I. Wherein the compounds of formulaI includes N-oxides, stereoisomers, tautomers and agriculturally orveterinarily acceptable salts thereof.

General Procedure:

With due modification of the starting compounds, the compounds offormula I can be prepared by procedures as given in below schemes.

The compounds of the formula (I) can be prepared by methods of organicchemistry, e.g, by the methods described herein after in schemes

General Procedure:

The compounds of the formula (I) can be prepared by the standard methodsof organic chemistry, e.g, by the methods described herein after inschemes 1 to 32 and in the synthesis description of the workingexamples. In the schemes 1 to 32, the radicals Ar, Q, W, A¹, A², A³ andR¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R^(ya), R^(zc), R^(yc), R^(yz),R¹ and R¹² are as defined above for compound of formula (I), unlessotherwise specified.

Compounds of formula (I), wherein Z is a single bond or —NR^(zc)—C(═S)—or —NR^(zc)—C(═O)— and T is O, N or N—R^(T), are the compounds offormula (Ia) and can be prepared by the methods described in WO2011/017504 or methods described in Scheme 1.

In one embodiment of Scheme 1, an aldehyde or ketone of the formula (II)is reacted with a compound of formula (E1) wherein Z is —NR^(zc)—C(═S)—or —NR^(zc)—C(═O)— and T is N, in the presence or in the absence of asolvent. Suitable solvents are polar protic solvents. If the reaction isperformed in the absence of a solvent, the compound of the formula (E1)usually also act as solvent. Compounds of the formula (E1) arecommercially available or can be prepared using standards organicreactions as described in March's Advanced Organic Chemistry 6thedition, Michael B. Smith and Jerry March.

According to another embodiment of Scheme 1, an aldehyde or ketonecompound of the formula (II) is first reacted with a hydrazine of theformula R^(zc)NHNH₂ followed by the reaction with an isocyanate of theformula R¹¹—NCO or with an isothiocyanate R¹¹—NCS to yield a compound ofthe formula (Ia), wherein Z is —N(R^(zc))—C(═O) or —N(R^(zc))—C(═S) andT is N.

According to another embodiment of Scheme 1, an aldehyde or ketonecompound of the formula (II) is first reacted with a hydroxylaminefollowed by the reaction with a compound R¹²-L, where L is a suitableleaving group, such as halogen or activated OH. Thereby, a compound ofthe formula (Ia) will result, wherein Z is a single bond and T is O.

According to another embodiment of the above reaction, an aldehyde orketone compound of formula (II) is first reacted with a hydroxylaminefollowed by reaction with an isocyanate of the formula R¹¹—NCO or withan isothiocyanate R¹¹—NCS to yield a compound of the formula (Ia),wherein Z is —O—C(═O)— or —O—C(═S)— and T is N.

Compounds of formula (Ia) in which Z is —NR^(zc)—C(═S)— or—NR^(zc)—C(═O)—, wherein C(═S) or C(═O) is bound to T and T is O, N orN—R^(T), can be prepared by analogy to the method described inSynthesis, 2010, 2990-296 or as shown in Scheme 2.

According to the method depicted in scheme 2, an isocyanate compound ofthe formula (IIa) is reacted with the compound of formula (E2) bystandard methods of isocyanate chemistry. The isocyanate of the formula(IIa) can be obtained e.g. via Lossen rearrangement of the correspondinghydroxamic acid (IVa). The hydroxamic acid (IVa) is reacted with1-propanephosphonic acid cyclic anhydride (T3P) in the presence of abase. The base is preferably N-methylmorpholine. The isocyanate of theformula (IIa) may also be obtained via Curtius rearrangement of thecorresponding azide of the formula (IVb), e.g. by analogy to the methoddescribed in WO 2014/204622.

For converting compounds of formula (Ia) and (Ib) in which R^(yz) orR^(zc) is H into compounds (I) in which R^(yz) or R^(zc) is differentfrom H, compounds of formula (Ia) and (Ib) in which R^(yz) or R^(zc) isH can be reacted with compounds of formulae R^(yz)-Lg or R^(zc)-Lgwherein R^(yz) or R^(zc) is not H and Lg is a leaving group, such as abromine, chlorine or iodine atom or a tosylate, mesylate or triflate, toyield compounds of formula (Ia) and (Ib), wherein R^(yz) or R^(zc) isdifferent from H. The reaction is suitably carried out in the presenceof a base such as sodium hydride or potassium hydride, suitably in apolar aprotic solvent such as N,N-dimethylformamide, tetrahydrofuran,dioxane, acetonitrile, dimethylsulfoxide or pyridine, or mixtures ofthese solvents, in a temperature range of from 0° C. and 100° C.

Compounds of the formula (Ic) can be prepared from compounds of formula(IIc) by the reactions shown below.

R^(11/12) corresponds to radicals R¹¹ or R¹² respectively. The reactionshown above can be performed by analogy to conventional methods ofpreparing carbamates. According to a first embodiment, the amine of theformula (IIc) is converted into either an isocyanate or p-nitrophenylcarbamate followed by treatment with an alcohol of the formula R¹¹—OH orR¹²—OH, respectively, in the presence of an organic or inorganic base.According to another embodiment, the compound of the formula (IIc) isreacted with a chloroformate of the formula R^(11/12)—O—C(═O)—Cl. Thechloroformate is prepared from the alcohols R^(11/12)—OH by treatmentwith phosgene or triphosgene in the presence of a base, e.g. pyridine.Compounds of formula (Ic), in which Z is —N(R^(zc))—C(═O)— or—N(R^(zc))—C(═S)— can be prepared by analogy to the methods described inWO 2013/009791 or by analogy to methods described in US 2012/0202687.

Compounds of formula (IIb) and (IIc) can be prepared from compounds offormula (IIa) by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Reaction step (i) can be performed byanalogy to method described in Journal of the American Chemical Society,124(22), 6343-6348, 2002. Reaction step (ii) cab be performed by analogyto method described in European Journal of Medicinal Chemistry, 49,310-323, 2012. Compounds of the formula (IIc) (reaction step (iii) ofthe above reaction) can be prepared by reacting compounds of the formula(IIa) with ammonia or amines of the formula R^(yc)NH₂ in the presence ofa metal catalyst or its salts, preferably copper or its salts asdescribed in Chem. Commun., 2009, 3035-3037.

Compounds of formula (IIa-1), where Q is —N(R²)—C(═S)— and W is N(R⁶)can be prepared by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Reaction step (iv) can be performed byanalogy to method described in WO2016200339. Step (v) involvesN-alkylation using respective alkyl halides with suitable bases likepotassium carbonate, as described in WO201150245. Step (vi) involvesoxidation of compounds of formula (IIe-2) using KMnO₄ as described inMarch's Advanced Organic Chemistry 6th edition, Michael B. Smith andJerry March. Step (vi) involves amide formation by reacting thecompounds of formula (IIe-3) with Ar—NHR² in presence of suitablecoupling reagent like HATU and base like DIPEA. Compounds of formula(IIa-1) can be prepared by reaction of compounds of formula (IIe-4) withP₂S₅ or Lawesson's reagent as described by, for example, Strong. et al,J. Med. Chem., 2017, 60, 5556-5585

Compounds of formula (Ig) are commercially available and can also beprepared from compounds of formula (IId) via Leimgruber-Batcho Indolesynthesis as described in RSV Advances, 4(9), 4672-4675, 2014, shownbelow.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate, preferably bromine. Compounds (IId) arecommercially available.

Compounds of formula (IIa-2), (IIa-2-1), (IIa-3) and (IIa-3-1) where Qis —N(R²)—C(═NR)— and W is N(R⁶) can be prepared by the reactions shownbelow.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Reaction step (ix) can be performed byanalogy to method described in Organic & Biomolecular Chemistry, 13,7257-7264, 2015. Step (x) involves N-alkylation using respective alkylhalides with suitable bases like potassium carbonate, as described inWO201150245. Reaction step (xi) can be performed by analogy to methoddescribed in WO2018126901. Step (xii) involves heating of compounds offormula (IIe-7) with Ar—NHR² in presence of trimethyl aluminium asdescribed in March's Advanced Organic Chemistry 6th edition, Michael B.Smith and Jerry March. Step (xiii) involves N-alkylation or N-arylationusing respective alkyl halides or aryl halides with suitable bases likepotassium carbonate, as described in WO201150245. Compounds of formula(IIa-3) can be prepared from compounds of formula (IIe-4) via generationof indazole-3-carboximidoyl chloride as intermediate using thionylchloride, then heating the intermediate with hydroxylamine hydrochlorideas described in March's Advanced Organic Chemistry 6th edition, MichaelB. Smith and Jerry March. Compounds of formula (IIa-3-1) can be preparedby heating compounds of formula R⁸-Lg (where Lg can be bromine,chlorine, tosylate, mesylate) in a polar protic or aprotic solvents withcompounds of formula (IIa-3) in an acidic, basic or neutral conditionsanalogous to methods, as described in WO2010129053, WO2007146824 orChemical Communications, 2014, 50, 1465.

Compounds of formula (IIa-4) and (IIa-4-1) where Q is —N═C(X)—; X is C₁or F and W is N(R⁶) can be prepared by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-4) can beprepared from compounds of formula (IIe-4) using thionyl chloride asdescribed in Angewandte Chemie International Edition, 53, 9068-9071,2014. Compounds of formula (IIa-4-1) can be prepared from compounds offormula (IIa-4) by a method described in Australian journal ofChemistry, 52, 807-811, 1999.

Compounds of formula (IIa-5), (IIa-6), (IIa-7) and (IIa-7-1) where Q is—N═C(X)—; X is OR⁸ or SR⁷ or N(R³)₂ or NH₂CN and W is N(R⁶) can beprepared by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-5), (IIa-6),(IIa-7) and (IIa-7-1) can be prepared by heating compounds of formula(IIa-4) with compounds of the formula R⁸—OH or R⁷—SH or NH(R³)₂ or NH₂CNin a polar protic or aprotic solvents in an acidic, basic or neutralconditions as described in WO2010129053, WO2007146824 or ChemicalCommunications, 2014, 50, 1465.

Compounds of formula (IIa-8), (IIa-9) and (IIa-10) where Q is —N═C(X)—;X is H or CN or C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,C3-C6-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkylmoieties are unsubstituted or substituted with halogen; phenyl, or —CH₂—phenyl, wherein the phenyl rings are unsubstituted or substituted withR⁵ and W is N(R⁶) can be prepared by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-8) can beeasily prepared by treating compounds of formula (IIe-2) with Ar—NH₂ asdescribed in March's Advanced Organic Chemistry 6th edition, Michael B.Smith and Jerry March. Steps (xxii) and (xxiii) involve Weinreb ketonesynthesis. Compounds of formula (IIa-9) can be easily prepared bytreating compounds of formula (IIe-4) with Ar—NH₂ as described inMarch's Advanced Organic Chemistry 6th edition, Michael B. Smith andJerry March. Reaction step (xxv) can be performed by analogy to methoddescribed in Chemistry A European Journal, 19, 11199-11202, 2013.

Compounds of formula (IIa-11) and (IIa-12) where Q is —N═C(X)—; X is—CR⁴═N(OCH₃) and W is N(R⁶) can be prepared by the reactions shownbelow.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Reaction step (xxvi) can be performed byanalogy to method described in Advanced Synthesis & Catalysis, 359(20),3665-3673, 2017. Step (xxvii) involves the formation of imine bytreating compounds of formula (IIe-10) with Ar—NH₂ as described inMarch's Advanced Organic Chemistry 6th edition, Michael B. Smith andJerry March. Steps (xxviii) and (xxix) involve Weinreb ketone synthesisvia Weinreb amide. Compounds of formula (IIa-11) can be prepared byheating the compounds of formula (IIe-13) with methylhydroxylaminehydrochloride as described in March's Advanced Organic Chemistry 6thedition, Michael B. Smith and Jerry March. Reaction step (xxxi) can beperformed by analogy to method described in Journal of ChemicalResearch, 41(6), 321-324, 2017. Compounds of formula (IIa-12) can beprepared by heating the compounds of formula (IIe-14) withmethylhydroxylamine hydrochloride as described in March's AdvancedOrganic Chemistry 6th edition, Michael B. Smith and Jerry March.

Compounds of formula (IIa-13) where Q is —N(R²)—C(═S)— and W is O or Scan be prepared as per below reactions.

In the above scheme, -Hal is fluorine, chlorine, bromine or iodine,preferably bromine. Step (xxxiii) involves amide formation by reactingthe compounds of formula (IIf) with Ar—NHR² in presence of suitablecoupling reagent like HATU and base like DIPEA. Compounds of formula(IIa-13) can be prepared by reaction of compounds of formula (IIe-4-1)with P₂S₅ or Lawesson's reagent as described by, for example, Strong. etal, J. Med. Chem., 2017, 60, 5556-5585.

Compounds of formula (IIf) are commercially available and can also beprepared from compounds of formula (IIh) by the reactions shown below.Compounds of formula (IIh) are commercially available.

In the above reactions, -Hal is fluorine, chlorine, bromine or iodine,preferably bromine. And -Hal′ is fluorine, chlorine, bromine or iodine,preferably fluorine. In the above scheme, step (xxxv) involvestransformation of ester to methyl ketone via Weinreb ketone synthesis.Step (xxxvi) involves oxime formation by refluxing ketone with NH₂OH.HClin protic solvent like MeOH analogous to the method, as described inMedicinal Chemistry Research, 25(3), 449-455, 2016. Step (xxxvii)involves base catalysed cyclization analogous to the method, asdescribed in WO2015/042397. Step (xxxviii) involves SeO₂ oxidation ofmethyl group to aldehyde as described in European Journal of MedicinalChemistry, 84, 42-50, 2014. Step (xxxix) involves standard oxidationreaction analogous to the method, as described in March's AdvancedOrganic Chemistry 6th edition, Michael B. Smith and Jerry March. Step(xl) involves transformation of oxime to thioxime using Lawesson'sreagent as described in Phosphorus, Sulfur and Silicon and the RelatedElements, 184(9), 2408-2426, 2009. Steps (xli), (xlii) and (xliii)analogous to steps (xxxvii), (xxxviii) and (xxxix).

Compounds of formula (IIa-14), (IIa-14-1), (IIa-15) and (IIa-15-1) whereQ is —N(R²)—C(═NR)— and W is O or S can be prepared by the reactionsshown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Reaction step (xliv) can be performed byanalogy to method described in Organic & Biomolecular Chemistry, 13,7257-7264, 2015. Reaction step (xlv) can be performed by analogy tomethod described in WO2018126901. Step(xlvi) involves heating ofcompounds of formula (IIk-2) with Ar—NHR² in presence of trimethylaluminium as described in March's Advanced Organic Chemistry 6thedition, Michael B. Smith and Jerry March. Step (xlvii) involvesN-alkylation or N-arylation using respective alkyl halides or arylhalides with suitable bases like potassium carbonate, as described inWO201150245. Compounds of formula (IIa-15) can be prepared fromcompounds of formula (IIj) via generation ofbenzisoxazole-3-carboximidoyl chloride orbenzisothiazole-3-carboximidoyl chloride as intermediate using thionylchloride, then heating the intermediate with hydroxylamine hydrochlorideas described in March's Advanced Organic Chemistry 6th edition, MichaelB. Smith and Jerry March. Compounds of formula (IIa-15-1) can beprepared by heating compounds of formula R⁸-Lg (where Lg can be bromine,chlorine, tosylate, mesylate) in a polar protic or aprotic solvents withcompounds of formula (IIa-15) in an acidic, basic or neutral conditionsanalogous to methods, as described in WO2010129053, WO2007146824 orChemical Communications, 2014, 50, 1465.

Compounds of formula (IIk) are commercially available and can also beprepared from compounds of formula (IIh) by the reactions shown below.Compounds of formula (IIh) are commercially available.

In the above reactions, -Hal is fluorine, chlorine, bromine or iodine,preferably bromine. And -Hal′ is fluorine, chlorine, bromine or iodine,preferably fluorine. Step (I) involves the standard reduction asdescribed in March's Advanced Organic Chemistry 6th edition, Michael B.Smith and Jerry March. Steps (li), (lii), (liii) and (liv) are analogousthe steps (xxxvi), (xxxvii), (xl) and (xli) as described in scheme 13.

Compounds of formula (IIa-16) and (IIa-16-1) where Q is —N═C(X)—; X isCl or F and W is O or S can be prepared by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-16) can beprepared from compounds of formula (IIj) using thionyl chloride asdescribed in Angewandte Chemie International Edition, 53, 9068-9071,2014. Compounds of formula (IIa-16-1) can be prepared from compounds offormula (IIa-16) by a method described in Australian journal ofChemistry, 52, 807-811, 1999.

Compounds of formula (IIa-17), (IIa-18), (IIa-19) and (IIa-19-1) where Qis —N═C(X)—; X is OR⁸ or SR⁷ or N(R³)₂ or NH₂CN and W is O or S can beprepared by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-17), (IIa-18),(IIa-19) and (IIa-19-1) can be prepared by heating compounds of formula(IIa-16) with compounds of the formula R⁸—OH or R⁷—SH or NH(R³)₂ orNH₂CN in a polar protic or aprotic solvents in an acidic, basic orneutral conditions as described in WO2010129053, WO2007146824 orChemical Communications, 2014, 50, 1465.

Compounds of formula (IIa-20), (IIa-21) and (IIa-22) where Q is—N═C(X)—; X is H or CN or C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,C3-C6-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkylmoieties are unsubstituted or substituted with halogen; phenyl, or —CH₂—phenyl, wherein the phenyl rings are unsubstituted or substituted withR⁵ and W is O or S can be prepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-20) can beeasily prepared by treating compounds of formula (Ili) with Ar—NH₂ asdescribed in March's Advanced Organic Chemistry 6th edition, Michael B.Smith and Jerry March. Steps (lxi) and (lxii) involve Weinreb ketonesynthesis. Compounds of formula (IIa-21) can be easily prepared bytreating compounds of formula (III) with Ar—NH₂ as described in March'sAdvanced Organic Chemistry 6th edition, Michael B. Smith and JerryMarch. Reaction step (lxiv) can be performed by analogy to methoddescribed in Chemistry A European Journal, 19, 11199-11202, 2013.

Compounds of formula (IIa-23) where Q is —C(═S)—N(R²)— and W is N(R⁶)can be prepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Step (Ixv) involves amide formation byreacting the compounds of formula (IIn) with Ar—COOH in presence ofsuitable coupling reagent like HATU and base like DIPEA. Compounds offormula (IIa-23) can be prepared by reaction of compounds of formula(IIo) with P2S5 or Lawesson's reagent as described by, for example,Strong. et al, J. Med. Chem., 2017, 60, 5556-5585.

Compounds of formula (IIn) are commercially available and can also beprepared from compounds of formula (IIm) by reacting with substitutedhydrazines in protic solvents like EtOH and irradiating in microwave asdescribed in WO201054279 (shown in scheme 20).

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIm) arecommercially available.

Compounds of formula (IIa-24), (IIa-24-1), (IIa-25) and (IIa-25-1) whereQ is —C(═NR)—N(R²)— and W is N(R⁶) can be prepared as per belowreactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Step (Ixviii) involves N-alkylation orN-arylation using respective alkyl halides or aryl halides with suitablebases like potassium carbonate, as described in WO201150245. Step (lxix)involves heating of compounds of formula (IIn) with Ar—CN in presence oftrimethyl aluminium as described in March's Advanced Organic Chemistry6th edition, Michael B. Smith and Jerry March. Step (Ixx) is analogousto step (lxviii). Compounds of formula (IIa-25) can be prepared fromcompounds of formula (IIo) via generation of indazole-3-carboximidoylchloride as intermediate using thionyl chloride, then heating theintermediate with hydroxylamine hydrochloride as described in March'sAdvanced Organic Chemistry 6th edition, Michael B. Smith and JerryMarch. Compounds of formula (IIa-25-1) can be prepared by heatingcompounds of formula R⁸-Lg (where Lg can be bromine, chlorine, tosylate,mesylate) in a polar protic or aprotic solvents with compounds offormula (IIa-25) in an acidic, basic or neutral conditions analogous tomethods, as described in WO2010129053, WO2007146824 or ChemicalCommunications, 2014, 50, 1465.

Compounds of formula (IIa-26) and (IIa-27) where Q is —C(X)═N—; X is Hor CN or X is H or CN or C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,C3-C6-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkylmoieties are unsubstituted or substituted with halogen; phenyl, or—CH₂-phenyl, wherein the phenyl rings are unsubstituted or substitutedwith R5 and W is N(R⁶) can be prepared by the reactions shown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-28) can beeasily prepared by treating compounds of formula (In) with Ar—CHO orAr—CR as described in March's Advanced Organic Chemistry 6th edition,Michael B. Smith and Jerry March. Reaction step (xxiv) can be performedby analogy to method described in Chemistry A European Journal, 19,11199-11202, 2013.

Compounds of formula (IIa-28) and (IIa-28-1) where Q is —C(X)═N—; X isCl or F and W is N(R⁶) can be prepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-28) can beprepared from compounds of formula (IIo) using thionyl chloride asdescribed in Angewandte Chemie International Edition, 53, 9068-9071,2014. Compounds of formula (IIa-28-1) can be prepared from compounds offormula (IIa-28) by a method described in Australian journal ofChemistry, 52, 807-811, 1999.

Compounds of formula (IIa-29), (IIa-30), (IIa-31) and (IIa-31-1) where Qis —C(X)═N—; X is OR⁸ or SR⁷ or N(R³)₂ or —NHCN and W is N(R⁶) can beprepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-29), (IIa-30),(IIa-31) and (IIa-31-1) can be prepared by heating compounds of formula(IIa-28) with compounds of the formula R⁸—OH or R⁷—SH or NH(R³)₂ orNH₂CN in a polar protic or aprotic solvents in an acidic, basic orneutral conditions as described in WO2010129053, WO2007146824 orChemical Communications, 2014, 50, 1465.

Compounds of formula (IIa-32) where Q is —C(═S)—N(R²)— and W is S or Ocan be prepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Step (Ixxx) involves amide formation byreacting the compounds of formula (IIr) with Ar—COOH in presence ofsuitable coupling reagent like HATU and base like DIPEA. Compounds offormula (IIa-32) can be prepared by reaction of compounds of formula(IIs) with P2S5 or Lawesson's reagent as described by, for example,Strong. et al, J. Med. Chem., 2017, 60, 5556-5585.

Compounds of formula (IIr) are commercially available or can be preparedfrom commercially available compounds of formula (IIh) as per belowreactions.

In the above reaction -Hal is chlorine, bromine or iodine, preferablybromine. And -Hal′ is chlorine, fluorine, bromine or iodine, preferablyfluorine or chlorine. Compounds of formula (IIr-1) can be prepared fromcommercially available compounds of formula (IIh). Step (Ixxxii)involves standard reduction protocol using NaBH₄ as described in March'sAdvanced Organic Chemistry 6th edition, Michael B. Smith and JerryMarch. Step (Ixxxiii) involves transformation of alcohols to nitriles bytreating alcohols with tert-butyl hypochlorite in the presence of(2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO) as described inSynthesis, 2013, 45, 2155-2164. Step (Ixxxiv) involves one-potcyclization of ortho substituted benzonitriles to3-amino-1,2-benzisoxazoles as described in Tetrahedron Letters, Vol. 37,No. 17, 2885-2886, 1996. Steps (Ixxxv) and (lxxxvi) involve sequentialselective substitution of halide with Na₂S followed by oxidativecyclization as described in Journal of Medicinal Chemistry, 2016, 59,9906-9918. Step (Ixxxvii) involves halogenation as described in EuropeanJournal of Medicinal Chemistry, 123 (2016) 332-353. Step (Ixxxviii)involves amination as described in Chemistry A European Journal, 2015,21, 3701-3707.

Compounds of formula (IIa-33), (IIa-33-1), (IIa-34) and (IIa-34-1) whereQ is —C(═NR)—N(R²)— and W is O or S can be prepared as per belowreactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Step (Ixxxix) involves N-alkylation orN-arylation using respective alkyl halides or aryl halides with suitablebases like potassium carbonate, as described in WO201150245. Step (xc)involves heating of compounds of formula (IIr-3) with Ar—CN in presenceof trimethyl aluminium as described in March's Advanced OrganicChemistry 6th edition, Michael B. Smith and Jerry March. Step (xci) isanalogous to step (Ixxxix). Compounds of formula (IIa-34) can beprepared from compounds of formula (IIs) via generation ofbenzisoxazole-3-carboximidoyl chloride orbenzisothiazole-3-carboximidoyl chloride as intermediate using thionylchloride, then heating the intermediate with hydroxylamine hydrochlorideas described in March's Advanced Organic Chemistry 6th edition, MichaelB. Smith and Jerry March. Compounds of formula (IIa-34-1) can beprepared by heating compounds of formula R⁸-Lg (where Lg can be bromine,chlorine, tosylate, mesylate) in a polar protic or aprotic solvents withcompounds of formula (IIa-34) in an acidic, basic or neutral conditionsanalogous to methods, as described in WO2010129053, WO2007146824 orChemical Communications, 2014, 50, 1465.

Compounds of formula (IIa-35) and (IIa-36) where Q is —C(X)═N—; X is Hor CN or X is H or CN or C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,C3-C6-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkylmoieties are unsubstituted or substituted with halogen; phenyl, or—CH₂-phenyl, wherein the phenyl rings are unsubstituted or substitutedwith R⁵ and W is O or S can be prepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or lodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-35) can beeasily prepared by treating compounds of formula (IIr) with Ar—CHO orAr—COR¹⁰ as described in March's Advanced Organic Chemistry 6th edition,Michael B. Smith and Jerry March. Reaction step xcv) can be performed byanalogy to method described in Chemistry A European Journal, 19,11199-11202, 2013.

Compounds of formula (IIa-37) and (IIa-37-1) where Q is —C(X)═N—; X isCl or F and W is O or S can be prepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-37) can beprepared from compounds of formula (IIs) using thionyl chloride asdescribed in Angewandte Chemie International Edition, 53, 9068-9071,2014. Compounds of formula (IIa-37-1) can be prepared from compounds offormula (IIa-37) by a method described in Australian journal ofChemistry, 52, 807-811, 1999.

Compounds of formula (IIa-38), (IIa-39), (IIa-40) and (IIa-40-1) where Qis —C(X)═N—; X is OR⁸ or SR⁷ or N(R³)₂ or —NHCN and W is O or S can beprepared as per below reactions.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Compounds of formula (IIa-38), (IIa-39),(IIa-40) and (IIa-40-1) can be prepared by heating compounds of formula(IIa-37) with compounds of the formula R⁸—OH or R⁷—SH or NH(R³)₂ orNH₂CN in a polar protic or aprotic solvents in an acidic, basic orneutral conditions as described in WO2010129053, WO2007146824 orChemical Communications, 2014, 50, 1465.

Compounds of formula (IIa-41) and (IIa-42) where Q is —N═C(X)—; X is—CR⁴═N(OCH₃) and W is O or S can be prepared by the reactions shownbelow.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesyl or triflate. Reaction step (ci) can be performed byanalogy to method described in Advanced Synthesis & Catalysis, 359(20),3665-3673, 2017. Step (cii) involves the formation of imine by treatingcompounds of formula (III-1) with Ar—NH₂ as described in March'sAdvanced Organic Chemistry 6th edition, Michael B. Smith and JerryMarch. Steps (ciii) and (civ) involve Weinreb ketone synthesis viaWeinreb amide. Compounds of formula (IIa-41) can be prepared by heatingthe compounds of formula (III-4) with methylhydroxylamine hydrochlorideas described in March's Advanced Organic Chemistry 6th edition, MichaelB. Smith and Jerry March. Reaction step (cvi) can be performed byanalogy to method described in Journal of Chemical Research, 41(6),321-324, 2017. Compounds of formula (IIa-42) can be prepared by heatingthe compounds of formula (III-5) with methylhydroxylamine hydrochlorideas described in March's Advanced Organic Chemistry 6th edition, MichaelB. Smith and Jerry March.

Compounds of formula (IIa-43) and (IIa-44) where Q is —C(X)═N—; X is—CR⁴═N(OCH₃) and W is N(R⁶) or O or S can be prepared by the reactionsshown below.

In the above reactions, -Hal is bromine, chlorine or iodine atom or atosylate, mesylate or triflate. Reaction step (cviii) involves theformation of imine as described in March's Advanced Organic Chemistry6th edition, Michael B. Smith and Jerry March. Steps (cix) and (cx)involve Weinreb ketone synthesis via Weinreb amide. Step (cxi), theformation of methyl oxime can be performed as described in March'sAdvanced Organic Chemistry 6th edition, Michael B. Smith and JerryMarch. Reaction step (cxii) can be performed by analogy to methoddescribed in Journal of Chemical Research, 41(6), 321-324, 2017. Step(cxiii) is analogous to step (cxi).

Individual compounds of formula I can also be prepared by derivatisationof other compounds of formula I or the intermediates thereof.

If the synthesis yields mixtures of isomers, a separation is generallynot necessarily required since in some cases the individual isomers canbe interconverted during work-up for use or during application (forexample under the action of light, acids or bases). Such conversions mayalso take place after use, for example in the treatment of plants in thetreated plant, or in the harmful fungus to be controlled.

A skilled person will readily understand that the preferences for thesubstituents, also in particular the ones given in the tables below forthe respective substituents, given herein in connection with compounds Iapply for the intermediates accordingly. Thereby, the substituents ineach case have independently of each other or more preferably incombination the meanings as defined herein.

Unless otherwise indicated, the term “compound(s) according to theinvention” or “compound(s) of the invention” or “compound(s) of formula(I)”, refers to the compounds of formula I.

The term “compound(s) according to the invention”, or “compounds offormula I” comprises the compound(s) as defined herein as well as astereoisomer, salt, tautomer or N-oxide thereof. The term “compound(s)of the present invention” is to be understood as equivalent to the term“compound(s) according to the invention”, therefore also comprising astereoisomer, salt, tautomer or N-oxide thereof.

The term “composition(s) according to the invention” or “composition(s)of the present invention” encompasses composition(s) comprising at leastone compound of formula I according to the invention as defined above.The compositions of the invention are preferably agricultural orveterinary compositions.

Depending on the substitution pattern, the compounds according to theinvention may have one or more centers of chirality, in which case theyare present as mixtures of enantiomers or diastereomers. The inventionprovides both the single pure enantiomers or pure diastereomers of thecompounds according to the invention, and their mixtures and the useaccording to the invention of the pure enantiomers or pure diastereomersof the compounds according to the invention or their mixtures. Suitablecompounds according to the invention also include all possiblegeometrical stereoisomers (cis/trans isomers) and mixtures thereof.

Cis/trans isomers may be present with respect to an alkene,carbon-nitrogen double-bond or amide group. The term “stereoisomer(s)”encompasses both optical isomers, such as enantiomers or diastereomers,the latter existing due to more than one center of chirality in themolecule, as well as geometrical isomers (cis/trans isomers). Thepresent invention relates to every possible stereoisomer of thecompounds of formula I. i.e. to single enantiomers or diastereomers, aswell as to mixtures thereof.

The compounds according to the invention may be amorphous or may existin one or more different crystalline states (polymorphs) which may havedifferent macroscopic properties such as stability or show differentbiological properties such as activities. The present invention relatesto amorphous and crystalline compounds according to the invention,mixtures of different crystalline states of the respective compoundsaccording to the invention, as well as amorphous or crystalline saltsthereof.

The term “tautomers” encompasses isomers, which are derived from thecompounds of formula I by the shift of an H-atom involving at least oneH-atom located at a nitrogen, oxygen or sulphur atom. Examples oftautomeric forms are keto-enol forms, imine-enamine forms, urea-isoureaforms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.

The term “stereoisomers” encompasses both optical isomers, such asenantiomers or diastereomers, the latter existing due to more than onecenter of chirality in the molecule, as well as geometrical isomers(cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. One center ofchirality is the carbon ring atom of the isothiazoline ring carryingradical R¹. The invention provides both the pure enantiomers ordiastereomers and their mixtures and the use according to the inventionof the pure enantiomers or diastereomers of the compound I or itsmixtures. Suitable compounds of the formula I also include all possiblegeometrical stereoisomers (cis/trans isomers) and mixtures thereof.

The term N-oxides relates to a form of compounds I in which at least onenitrogen atom is present in oxidized form (as NO). To be more precise,it relates to any compound of the present invention which has at leastone tertiary nitrogen atom that is oxidized to an N-oxide moiety.N-oxides of compounds I can in particular be prepared by oxidizing e.g.the ring nitrogen atom of an N-heterocycle, e.g. a pyridine orpyrimidine ring present in Ar or R¹¹, or an imino-nitrogen present incentral tricyclic core, with a suitable oxidizing agent, such as peroxocarboxylic acids or other peroxides. The person skilled in the art knowsif and in which positions compounds of the present invention may formN-oxides.

Salts of the compounds of the formula I are preferably agriculturallyand veterinarily acceptable salts. They can be formed in a customarymethod, e.g. by reacting the compound with an acid of the anion inquestion if the compound of formula I has a basic functionality or byreacting an acidic compound of formula I with a suitable base.

Suitable agriculturally or veterinarily acceptable salts are especiallythe salts of those cations or the acid addition salts of those acidswhose cations and anions, which are known and accepted in the art forthe formation of salts for agricultural or veterinary use respectively,and do not have any adverse effect on the action of the compoundsaccording to the present invention. Suitable cations are in particularthe ions of the alkali metals, preferably lithium, sodium and potassium,of the alkaline earth metals, preferably calcium, magnesium and barium,and of the transition metals, preferably manganese, copper, zinc andiron, and also ammonium (NH⁴) and substituted ammonium in which one tofour of the hydrogen atoms are replaced by C₁-C₄-alkyl,C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or —CH₂-phenyl. Examples ofsubstituted ammonium ions comprise methylammonium, isopropylammonium,dimethylammonium, diisopropylammonium, trimethylammonium,tetramethylammonium, tetraethylammonium, tetrabutylammonium,2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium,bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium andbenzyl-triethylammonium, furthermore phosphonium ions, sulfonium ions,preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium. Suitable acid addition veterinarilyacceptable salts, e.g. formed by compounds of formula I containing abasic nitrogen atom, e.g. an amino group, include salts with inorganicacids, for example hydrochlorides, sulphates, phosphates, and nitratesand salts of organic acids for example acetic acid, maleic acid,dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid,methane sulfonic acid, and succinic acid.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound of formulae I withan acid of the corresponding anion, preferably of hydrochloric acid,hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The term “invertebrate pest” as used herein encompasses animalpopulations, such as insects, arachnids and nematodes, which may attackplants, thereby causing substantial damage to the plants attacked, aswell as ectoparasites which may infest animals, in particular warmblooded animals such as e.g. mammals or birds, or other higher animalssuch as reptiles, amphibians or fish, thereby causing substantial damageto the animals infested.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e. g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants,including seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil. The plant propagationmaterials may be treated prophylactically with a plant protectioncompound either at or before planting or transplanting. Said youngplants may also be protected before transplantation by a total orpartial treatment by immersion or pouring.

The term “plants” comprises any types of plants including “modifiedplants” and in particular “cultivated plants”.

The term “modified plants” refers to any wild type species or relatedspecies or related genera of a cultivated plant.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or genetic engineeringincluding but not limiting to agricultural biotech products on themarket or in development (cf.http://www.bio.org/speeches/pubs/er/agri_products.asp). Geneticallymodified plants are plants, which genetic material has been so modifiedby the use of recombinant DNA techniques that under naturalcircumstances cannot readily be obtained by cross breeding, mutations ornatural recombination. Typically, one or more genes have been integratedinto the genetic material of a genetically modified plant in order toimprove certain properties of the plant. Such genetic modifications alsoinclude but are not limited to targeted posttranslational modificationof protein(s), oligo- or polypeptides e. g. by glycosylation or polymeradditions such as prenylated, acetylated or farnesylated moieties or PEGmoieties.

Plants that have been modified by breeding, mutagenesis or geneticengineering, e. g. have been rendered tolerant to applications ofspecific classes of herbicides, such as auxin herbicides such as dicambaor 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase(HPPD) inhibitors or phytoene desaturase (PDS) inhibittors; acetolactatesynthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones;enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such asglyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitorssuch as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e.bromoxynil or ioxynil) herbicides as a result of conventional methods ofbreeding or genetic engineering.

Furthermore, plants have been made resistant to multiple classes ofherbicides through multiple genetic modifications, such as resistance toboth glyphosate and glufosinate or to both glyphosate and a herbicidefrom another class such as ALS inhibitors, HPPD inhibitors, auxinherbicides, or ACCase inhibitors. These herbicide resistancetechnologies are e. g. described in Pest Managem. Sci. 61, 2005, 246;61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008,326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res.58, 2007, 708; Science 316, 2007, 1185; and references quoted therein.Several cultivated plants have been rendered tolerant to herbicides byconventional methods of breeding (mutagenesis), e. g. Clearfield® summerrape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant tosulfonyl ureas, e. g. tribenuron. Genetic engineering methods have beenused to render cultivated plants such as soybean, cotton, corn, beetsand rape, tolerant to herbicides such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance®(imidazolinone tolerant, BASF SE, Germany) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as δ-endotoxins, e. g. CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e. g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e. g. WO 02/015701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above. These insecticidal proteins contained in thegenetically modified plants impart to the plants producing theseproteins tolerance to harmful pests from all taxonomic groups ofathropods, especially to beetles (Coeloptera), two-winged insects(Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).Genetically modified plants capable to synthesize one or moreinsecticidal proteins are, e. g., described in the publicationsmentioned above, and some of which are commercially available such asYieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus(corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corncultivars producing the Cry9c toxin), Herculex® RW (corn cultivarsproducing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enyzme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis—related proteins” (PR proteins, see, e. g. EP-A 392 225),plant disease resistance genes (e. g. potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from themexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e. g. bio mass production, grain yield, starchcontent, oil content or protein content), tolerance to drought, salinityor other growth-limiting environmental factors or tolerance to pests andfungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e. g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera®rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e. g. potatoes that produce increased amounts of amylopectin(e. g. Amflora® potato, BASF SE, Germany).

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual members. The prefix C_(n)-C_(m) indicates in each casethe possible number of carbon atoms in the group.

The term halogen denotes in each case F, Br, Cl or I, in particular F, Cor Br.

The term “alkyl” as used herein and in the alkyl moieties of alkoxy,alkylthio, and the like refers to saturated straight-chain or branchedhydrocarbon radicals having 1 to 2 (“C₁-C₂-alkyl”), 1 to 3(“C₁-C₃-alkyl”), 1 to 4 (“C₁-C₄-alkyl”) or 1 to 6 (“C₁-C₆-alkyl”) carbonatoms. C₁-C₂-Alkyl is CH₃ or C₂H₅. C₁-C₃-Alkyl is additionally propyland isopropyl. C₁-C₄-Alkyl is additionally butyl, 1-methylpropyl(sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl(tert-butyl). C₁-C₆-Alkyl is additionally also, for example, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

The term “haloalkyl” as used herein, which is also expressed as “alkylwhich is partially or fully halogenated”, refers to straight-chain orbranched alkyl groups having 1 to 2 (“C₁-C₂-haloalkyl”), 1 to 3(“C₁-C₃-haloalkyl”), 1 to 4 (“C₁-C₄-haloalkyl”) or 1 to 6(“C₁-C₆-haloalkyl”) carbon atoms (as mentioned above), where some or allof the hydrogen atoms in these groups are replaced by halogen atoms asmentioned above: in particular C₁-C₂-haloalkyl, such as chloromethyl,bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.C₁-C₃-haloalkyl is additionally, for example, 1-fluoropropyl,2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl,1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl,heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and thelike. Examples for C₁-C₄-haloalkyl are, apart those mentioned forC₁-C₃-haloalkyl, 4-chlorobutyl and the like.

The term “alkylene” (or alkanediyl) as used herein in each case denotesan alkyl radical as defined above, wherein one hydrogen atom at anyposition of the carbon backbone is replaced by one further binding site,thus forming a bivalent moiety. Alkylene has preferably 1 to 6 carbonatoms (C₁-C₆-alkylene), 2 to 6 carbon atoms (C₂-C₆-alkylene), inparticular 1 to 4 carbon atoms (C₁-C₄-alkylene) or 2 to 4 carbon atoms(C₂-C₄-alkylene). Examples of alkylene are methylene (CH2),1,1-ethandiyl, 1,2-ethandiyl, 1,3-propandiyl, 1,2-propandiyl,2,2-propandiyl, 1,4-butandiyl, 1,2-butandiyl, 1,3-butandiyl,2,3-butandiyl, 2,2-butandiyl, 1,5-pentandiyl,2,2-dimethylpropan-1,3-diyl, 1,3-dimethyl-1,3-propandiyl, 1,6-hexandiyletc.

The term “alkenyl” as used herein refers to monounsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-alkenyl”), 2 to 4 (“C₂-C₄-alkenyl”) or 2 to 6 (“C₂-C₆-alkenyl)carbon atoms and a double bond in any position, for exampleC₂-C₃-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl or1-methylethenyl; C₂-C₄-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl,1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl;C₂-C₆-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl,1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl,1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl,5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl,3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl,1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl,3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl,1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl,2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl,1-ethyl-2-methyl-2-propenyl and the like.

The term “alkynyl” as used herein refers to straight-chain or branchedhydrocarbon groups having 2 to 3 (“C₂-C₃-alkynyl”), 2 to 4(“C₂-C₄-alkynyl”) or 2 to 6 (“C₂-C₆-alkynyl”) carbon atoms and one ortwo triple bonds in any position, for example C₂-C₃-alkynyl, such asethynyl, 1-propynyl or 2-propynyl; C₂-C₄-alkynyl, such as ethynyl,1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl and the like, C₂-C₆-alkynyl, such as ethynyl,1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl andthe like;

The term “cycloalkyl” as used herein refers to mono- or bi- orpolycyclic saturated hydrocarbon radicals having in particular 3 to 6(“C₃-C₆-cycloalkyl”) or 3 to 5 (“C₃-C₅-cycloalkyl”) or 3 to 4(“C₃-C₄-cycloalkyl”) carbon atoms. Examples of monocyclic radicalshaving 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl. Examplesof monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl,cyclobutyl and cyclopentyl. Examples of monocyclic radicals having 3 to6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atomscomprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyland cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atomscomprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyland bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes amonocyclic saturated hydrocarbon radical.

The term “cycloalkoxy” as used herein refers to a cycloalkyl radical, inparticular a monocyclic cycloalkyl radical, as defined above having inparticular 3 to 6 (“C₃-C₆-cycloalkoxy”) or 3 to 5 (“C₃-C₅-cycloalkoxy”)or 3 to 4 (“C₃-C₄-cycloalksoxy”) carbon atoms, which is bound via anoxygen atom to the remainder of the molecule.

The term “cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₈-cycloalkyl(“C₃-C₈-cycloalkyl-C₁-C₄-alkyl”), preferably a C₃-C₆-cycloalkyl(“C₃-C₆-cycloalkyl-C₁-C₄-alkyl”), more preferably a C₃-C₄-cycloalkyl(“C₃-C₄-cycloalkyl-C₁-C₄-alkyl”) as defined above (preferably amonocyclic cycloalkyl group) which is bound to the remainder of themolecule via a C₁-C₄-alkyl group, as defined above. Examples forC₃-C₄-cycloalkyl-C₁-C₄-alkyl are cyclopropylmethyl, cyclopropylethyl,cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl andcyclobutylpropyl, Examples for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, apart thosementioned for C₃-C₄-cycloalkyl-C₁-C₄-alkyl, are cyclopentylmethyl,cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyland cyclohexylpropyl.

The term “C₁-C₂-alkoxy” is a C₁-C₂-alkyl group, as defined above,attached via an oxygen atom. The term “C₁-C₃-alkoxy” is a C₁-C₃-alkylgroup, as defined above, attached via an oxygen atom. The term“C₁-C₄-alkoxy” is a C₁-C₄-alkyl group, as defined above, attached via anoxygen atom. The term “C₁-C₆-alkoxy” is a C₁-C₆-alkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₁₀-alkoxy” is aC₁-C₁₀-alkyl group, as defined above, attached via an oxygen atom.C₁-C₂-Alkoxy is OCH₃ or OC₂H₅. C₁-C₃-Alkoxy is additionally, forexample, n-propoxy and 1-methylethoxy (isopropoxy). C₁-C₄-Alkoxy isadditionally, for example, butoxy, 1-methylpropoxy (sec-butoxy),2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy).C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy. C₁-C₆-Alkoxy is additionally, for example,heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.C₁-C₁₀-Alkoxy is additionally, for example, nonyloxy, decyloxy andpositional isomers thereof.

The term “C₁-C₂-haloalkoxy” is a C₁-C₂-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₃-haloalkoxy” is aC₁-C₃-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₄-haloalkoxy” is a C₁-C₄-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₆-haloalkoxy” is aC₁-C₆-haloalkyl group, as defined above, attached via an oxygen atom.C₁-C₂-Haloalkoxy is, for example, OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂,OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC₂F5.C₁-C₃-Haloalkoxy is additionally, for example, 2-fluoropropoxy,3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,OCH₂—C₂F5, OCF₂—C₂F5, 1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxyor 1-(CH₂Br)-2-bromoethoxy. C₁-C₄-Haloalkoxy is additionally, forexample, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy ornonafluorobutoxy. C₁-C₆-Haloalkoxy is additionally, for example,5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy,undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy,6-iodohexoxy or dodecafluorohexoxy.

The term “C₁-C₆-alkoxy-C₁-C₄-alkyl” as used herein, refers to astraight-chain or branched alkyl having 1 to 4 carbon atoms, as definedabove, where one hydrogen atom is replaced by a C₁-C₆-alkoxy group, asdefined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl,1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl,1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl,2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl,2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl,1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl,1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl,2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl,2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl,3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl,3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl,3-tert-butoxypropyl and the like.

The term “alkoxyalkoxy” as used herein refers to an alkoxyalkyl radical,in particular a C₁-C₆-alkoxy-C₁-C₄-alkyl radical, as defined above,which is bound via an oxygen atom to the remainder of the molecule.Examples thereof are OCH₂—OCH₃, OCH₂—OC₂H₅, n-propoxymethoxy,OCH₂—OCH(CH3)₂, n-butoxymethoxy, (1-methylpropoxy)methoxy,(2-methylpropoxy)methoxy, OCH₂—OC(CH3)₃, 2-(methoxy)ethoxy,2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy,2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy,2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, etc.

The substituent “oxo” replaces a CH₂ by a C(═O) group.

The term “aryl” relates to phenyl and bi- or polycyclic carbocycleshaving at least one fused phenylene ring, which is bound to theremainder of the molecule. Examples of bi- or polycyclic carbocycleshaving at least one phenylene ring include naphthyl, tetrahydronaphthyl,indanyl, indenyl, anthracenyl, fluorenyl etc.

The term “aryl-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as defined above,wherein one hydrogen atom has been replaced by an aryl radical, inparticular a phenyl radical. Particular examples of aryl-C₁-C₄-alkylinclude —CH₂-phenyl, 1-phenethyl, 2-phenetyl, 1-phenylpropyl,2-phenylpropyl, 3-phenyl-1-propyl and 2-phenyl-2-propyl.

The term “aryloxy-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as defined above,wherein one hydrogen atom has been replaced by an aryloxy radical, inparticular a phenoxy radical. Particular examples of aryloxy-C₁-C₄-alkylinclude phenoxymethyl, 1-phenoxyethyl, 2-phenoxyetyl, 1-phenoxypropyl,2-phenoxypropyl, 3-phenoxy-1-propyl and 2-phenoxy-2-propyl.

The term “aryl-C₁-C₄-carbonyl” relates to aryl as defined above, inparticular a phenyl radical, which is bound by a carbonyl to theremainder of the molecule. Particular examples of arylcarbonyl includebenzoyl, 1-naphthoyl and 2-naphthoyl.

The term “hetaryl” relates to aromatic heterocycles having either 5 or 6ring atoms (5- or 6-membered hetaryl) and being monocyclic or 8, 9 or 10ring atoms and bing bicyclic. Hetaryl will generally have at least onering atom selected from O, S and N, which in case of N may be animino-nitrogen or an amino-nitrogen, which carries hydrogen or a radicaldifferent from hydrogen. Hetaryl may have 1, 2, 3 or 4 further nitrogenatoms as ring members, which are imino nitrogens. Examples of 5- or6-membered hetaryl include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl,4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl,2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl,4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl,1,3,4-oxadiazolyl-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl and 1,3,5-triazin-2-yl. Examples of 8-, 9- or10-membered hetaryl include, for example, quinolinyl, isoquinolinyl,cinnolinyl, indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl,benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl,benzimidazolyl, imidazo[1,2-a]pyridine-2-yl, thieno[3,2-b]pyridine-5-yl,imidazo-[2,1-b]-thiazol-6-yl and 1,2,4-triazolo[1,5-a]pyridine-2-yl.

Examples of N-bound 5-, 6-, 7 or 8-membered saturated heterocyclesinclude: pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl,oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl,isothiazolidin-2-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl,thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl,1,1-dioxothiomorpholin-4-yl, azepan-1-yl and the like.

The term “hetaryl-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as defined above,wherein one hydrogen atom has been replaced by a hetaryl radical, inparticular a pyridyl radical. Particular examples of hetaryl-C₁-C₄-alkylinclude 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl,1-(2-pyridyl)ethyl, 2-(2-pyridyl)ethyl, 1-(3-pyridyl)ethyl,2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4-pyridyl)ethyl etc.

The term “hetaryloxy-C₁-C₄-alkyl” relates to C₁-C₄-alkyl, as definedabove, wherein one hydrogen atom has been replaced by an hetaryloxyradical, in particular a pyridyloxy radical. Particular examples ofhetaryloxy-C₁-C₄-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl,4-pyridyloxymethyl, 1-(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl,1-(3-pyridyloxy)ethyl, 2-(3-pyridyloxy)ethyl, 1-(4-pyridyloxy)ethyl,2-(4-pyridyloxy)ethyl etc.

The term “hetaryl-C₁-C₄-carbonyl” relates to hetaryl as defined above,in particular a C-bound hetaryl radical, e.g. 2-, 3- or 4-pyridyl, 2- or3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl,pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl radical,which is bound by a carbonyl to the remainder of the molecule.

The term “substituted” if not specified otherwise refers to substitutedwith 1, 2 or maximum possible number of substituents. If substituents asdefined in compounds of formula I are more than one then they areindependently from each other are same or different if not mentionedotherwise.

With respect to the variables, the embodiments of the compounds of theformula I are,

In one preferred embodiment, W is O.

In another preferred embodiment, W is NR⁶.

In another preferred embodiment, W is S(═O)_(m).

In one preferred embodiment, A¹ is CR^(A).

In another preferred embodiment, A¹ is N.

In one preferred embodiment, A² is CR^(B1).

In another preferred embodiment, A² is N.

In one preferred embodiment, A³ is CR^(B1).

In another preferred embodiment, A³ is N.

In one preferred embodiment, W is O, A¹ is CR^(A), A² is CR^(B), and A³is N.

In another preferred embodiment, W is O, A¹ is CR^(A), A² is CR^(B), andA³ is CR^(B1).

In another preferred embodiment, W is O, A¹ is N, A² is N, and A³ isR^(B1).

In another preferred embodiment, W is O, A¹ is CR^(A), A² is N, and A³is R^(B1).

In another preferred embodiment, W is O, A¹ is N, A² is CR^(B), and A³is R^(B1).

In another preferred embodiment, W is O, A¹ is CR^(A), A² is N, and A³is N.

In another preferred embodiment, W is N, A¹ is CR^(A), A² is CR^(B), andA³ is N.

In another preferred embodiment, W is N, A¹ is CR^(A), A² is CR^(B), andA³ is CR^(B1).

In another preferred embodiment, W is N, A¹ is N, A² is N, and A³ isCR^(B1).

In another preferred embodiment, W is N, A¹ is CR^(A), A² is N, and A³is R^(B1).

In another preferred embodiment, W is N, A¹ is N, A² is CR^(B), and A³is R^(B1).

In another preferred embodiment, W is N, A¹ is CR^(A), A² is N, and A³is N.

In another preferred embodiment, W is S(═O)_(m), A¹ is CR^(A), A² isCR^(B), and A³ is N.

In another preferred embodiment, W is S(═O)_(m), A¹ is CR^(A), A² isCR^(B), and A³ is CR^(B1).

In another preferred embodiment, W is S(═O)_(m), A¹ is N, A² is N, andA³ is R^(B1).

In another preferred embodiment, W is S(═O)_(m), A¹ is CR^(A), A² is N,and A³ is R^(B1).

In another preferred embodiment, W is S(═O)_(m), A¹ is N, A² is CR^(B),and A³ is R^(B1).

In another preferred embodiment, W is S(═O)_(m), A¹ is CR^(A), A² is N,and A³ is N.

In another preferred embodiment, wherein W is N or S(═O)_(m), A¹ and A²are CH, or A³ is CH or N;

In one preferred embodiment, R^(A) is H, halogen, OH, CN, NO₂, —SCN,—SF₅, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₂-C₆-alkenyl, or tri-C₁-C₆-alkylsilyl.

In more preferred embodiment, R^(A) is H, halogen, OH, CN, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, ortri-C₁-C₆-alkylsilyl.

In most preferred embodiment, R^(A) is H, Cl, Br, F, OH, CN, CH₃, C₂H₅,n-C₃H₇, isopropyl, cyclopropyl, allyl and propargyl, CH₂F, CHF₂, CF₃,OCH₃, OC₂H₅, OCH₂F, OCHF₂, OCF₃, OCH₂CH₂CF₃, OCH₂CF₂CHF₂, or OCH₂CF₂CF₃.

In one preferred embodiment, R^(B) is H, halogen, OH, CN, NO₂, —SCN,—SF₅, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₂-C₆-alkenyl, or tri-C₁-C₆-alkylsilyl.

In more preferred embodiment, R^(B) is H, halogen, OH, CN, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, ortri-C₁-C₆-alkylsilyl.

In most preferred embodiment, R^(B) is H, Cl, Br, F, OH, CN, CH₃, C₂H₅,n-C₃H₇, isopropyl, cyclopropyl, allyl and propargyl, CH₂F, CHF₂, CF₃,OCH₃, OC₂H₅, OCH₂F, OCHF₂, OCF₃, OCH₂CH₂CF₃, OCH₂CF₂CHF₂, or OCH₂CF₂CF₃.

In one preferred embodiment, R^(B1) is H, halogen, OH, CN, NO₂, —SCN,—SF₅, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₂-C₆-alkenyl, or tri-C₁-C₆-alkylsilyl.

In more preferred embodiment, R^(B1) is H, halogen, OH, CN, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, ortri-C₁-C₆-alkylsilyl.

In most preferred embodiment, R^(B1) is H, C, Br, F, OH, CN, CH₃, C₂H₅,n-C₃H₇, isopropyl, cyclopropyl, allyl and propargyl, CH₂F, CHF₂, CF₃,OCH₃, OC₂H₅, OCH₂F, OCHF₂, OCF₃, OCH₂CH₂CF₃, OCH₂CF₂CHF₂, or OCH₂CF₂CF₃.

In one preferred embodiment, Q is —N═C(X)—, —N(R²)—C(═NR)—, or—N(R²)—C(═S)—, or tautomers thereof wherein Ar is bound to either sideof Q;

In another preferred embodiment, Q is —N═C(X)—, or —N(R²)—C(═NR)—, ortautomers thereof wherein Ar is bound to either side of Q;

In another preferred embodiment, Q is —N═C(X)—, wherein N is bound toAr.

In another preferred embodiment, Q is —N═C(X)—, wherein C is bound toAr.

In another preferred embodiment, Q is —N(R²)—C(═NR)—, wherein N is boundto Ar.

In another preferred embodiment, Q is —N(R²)—C(═NR)—, wherein C is boundto Ar.

In another preferred embodiment, Q is —N(R²)—C(═S)—, wherein N is boundto Ar.

In another preferred embodiment, Q is —N(R²)—C(═S)—, wherein C is boundto Ar.

Preferred X is H, halogen, SR⁷, OR⁸, N(R³)₂, —CR⁴═N(OCH₃), CN,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl;

also preferred X is H, halogen, SR⁷, OR⁸, N(R³)₂, CN, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl;

also preferred X is H, halogen, SR⁷, or N(R³)₂;

also referred X is H, halogen, S(C₁-C₆-alkyl), C₁-C₆-alkoxy, N(R³)₂,—CR⁴═N(OCH₃), CN, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl,or C₃-C₆-halocycloalkyl;

also preferred X is phenyl, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R⁵:

particularly preferred X is H, CH₃, C₂H₅, CN, F, C₁, CF₃, OCH₃, OC₂H₅,OCH₂COOC₂H₅, NHCH₃, —R⁴C═N(OCH₃), NHC₂H₅, NCH₂COO C₂H₅, SCH₃, SC₂H₅,SCH₂COOEt, —CH₂-phenyl, phenyl wherein phenyl is substituted withhalogens, OCF₃, CF₃, CN, NO₂, alkyl, thioalkyl, alkoxy; and wherein R⁴is H, CH₃, C₂H₅, —CH₂-phenyl, phenyl wherein phenyl is substituted withhalogen, CF₃, OCF₃, SF₃, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-thioalkyl,C₁-C₆-alkoxy;

Preferred R is H, CN, C₁-C₆-alkyl, SR⁷, OR⁸, N(R³)₂, phenyl, or—CH₂-phenyl, wherein the phenyl rings are unsubstituted or substitutedwith R⁵;

Also preferred R is H, CN, C₁-C₆-alkyl, or OR⁸;

More preferred R is CH₃, C₂H₅, CN, OCH₃, OC₂H₅, OCH₂COOC₂H₅, NHCH₃,NHC₂H₅, NHCH₂COOC₂H₅, SCH₃, SC₂H₅, SCH₂COOC₂H₅, —CH₂-phenyl, phenylwhere in phenyl is substituted with halogens, CF₃, OCF₃, SF₃, CN, NO₂,C₁-C₆-alkyl, C₁-C₆-thioalkyl, C₁-C₆-alkoxy;

In one preferred embodiment, R³, R⁶ are, identical or different, H,C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl,C(═O)—OR^(a), C₁-C₆-alkyl-C(═O)—OR^(a), C(═O)—NR^(b)R^(c), C(═O)—R^(d),SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein thephenyl rings are unsubstituted or substituted with R^(f);

In more preferred embodiment, R³, R⁶ are, identical or different, H,C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C(═O)—OR^(a), C₁-C₆-alkyl-C(═O)—OR^(a),C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, or —CH₂-phenyl, wherein thephenyl rings are unsubstituted or substituted with R^(f);

In most preferred embodiment, R³, R⁶ are, identical or different, H,C₁-C₆-alkyl, or C₁-C₆-haloalkylalkyl;

In one preferred embodiment, R⁴ is H, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkylalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl,C(═O)—OR^(a), C₁-C₆-alkyl-C(═O)—OR^(a), C(═O)—NR^(b)R^(c), C(═O)—R^(d),SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein thephenyl rings are unsubstituted or substituted with R^(f);

In more preferred embodiment, R⁴ is H, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkylalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C(═O)—OR^(a), C₁-C₆-alkyl-C(═O)—OR^(a), C(═O)—NR^(b)R^(c), C(═O)R^(d),phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted orsubstituted with R^(f); In most preferred embodiment, R⁴ is H, halogen,C₁-C₆-alkyl, or C₁-C₆-haloalkylalkyl;

In one preferred embodiment R⁷ is C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, C(═O)—OR^(a), C₁-C₆-alkyl-C(═O)—OR^(a),C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, or —CH₂-phenyl, wherein thephenyl rings are unsubstituted or substituted with R^(f);

In more preferred embodiment, R⁷ is C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C(═O)—OR^(a),C₁-C₆-alkyl-C(═O)—OR^(a), C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, or—CH₂-phenyl, wherein the phenyl rings are unsubstituted or substitutedwith R^(f);

In most preferred embodiment R⁷ is C₁-C₆-alkyl, or C₁-C₆-haloalkylalkyl;

In preferred embodiment, R⁸ is C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, C(═O)—OR^(a), C₁-C₆-alkyl-C(═O)—OR^(a),C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl,or —CH₂-phenyl, wherein the phenyl rings are unsubstituted orsubstituted with R^(f);

In more preferred embodiment, R⁸ is C₁-C₆-alkyl, C₁-C₆-haloalkylalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C(═O)—OR^(a),C₁-C₆-alkyl-C(═O)—OR^(a), C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, orCH₂-phenyl, wherein the phenyl rings are unsubstituted or substitutedwith R^(f);

In most preferred embodiment, R⁸ is halogen, C₁-C₆-alkyl, orC₁-C₆-haloalkylalkyl;

In a preferred embodiment, R² is H, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, or C₃-C₆-cycloalkyl, which areunsubstituted or substituted with halogen,

In one preferred embodiment, Ar is phenyl which is unsubstituted orsubstituted with R^(Ar).

In another preferred embodiment, Ar is 5- or 6-membered hetaryl, whichis unsubstituted or substituted with R^(Ar).

In more preferred embodiment, Ar is phenyl, pyrimidinyl, pyridazinyl, orpyridyl, which are unsubstituted or substituted with R^(Ar).

Also in more preferred embodiment, Ar is phenyl, or pyridyl, which areunsubstituted or substituted with R^(Ar).

Also in more preferred embodiment, Ar is phenyl, which is unsubstitutedor substituted with R^(Ar).

Also in more preferred embodiment, Ar is pyridyl, which is unsubstitutedor substituted with R^(Ar).

In one preferred embodiment, R^(Ar) is halogen, OH, CN, NO₂, SCN,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, orS—R^(e).

In another preferred embodiment, R^(Ar) is halogen, C₁-C₆-haloalkyl, orC₁-C₆-haloalkoxy.

In more preferred embodiment, R^(Ar) is F, C, Br, OH, CN, NO₂, SCN, CH₃,C₂H₅, n-C₃H₇, isopropyl, CH₂F, CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅,CH₂CH₂CF₃, CH₂CF₂CHF₂, CH₂CF₂CF₃, OCH₃, OC₂H₅, n-propyloxy,isopropyloxy, OCH₂F, OCHF₂, OCF₃, OCH₂CF₃, OCF₂CHF₂, OC₂F₅, OCH₂CH₂CF₃,OCH₂CF₂CHF₂, OCH₂CF₂CF₃, or S—R^(e), where R^(e) is C₁-C₆-alkyl, inparticular C₁-C₃-alkyl such as CH₃, C₂H₅, n-C₃H₇ or isopropyl, orC₁-C₆-haloalkyl, in particular fluorinated C₁-C₃-alkyl such as CH₂F,CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅, CH₂CH₂CF₃, CH₂CF₂CHF₂ or CH₂CF₂CF₃.

Particularly preferred Ar are listed in Table A below.

TABLE A

Ar-1

Ar-2

Ar-3

Ar-4

Ar-5

Ar-6

Ar-7

Ar-8

Ar-9

Ar-10

Ar-11

Ar-12

Ar-13

Ar-14

More particularly preferred Ar is Ar-1, Ar-2, Ar-3, Ar-10, Ar-13, orAr-14

In one preferred embodiment, R¹ is Y—Z-T-R¹¹.

In another preferred embodiment, R¹ is Y—Z-T-R¹².

In one preferred embodiment, Y is —CR^(ya)═N—, wherein the N is bound toZ.

In another preferred embodiment, Y is —NR^(yc)—C(═S)—, wherein C(═S) isbound to Z.

In another preferred embodiment, Y is —NR^(yc)—C(═O)—, wherein C(═O) isbound to Z.

In one preferred embodiment, Z is —NR^(zc)—C(═S)—, wherein C(═S) isbound to T.

In another preferred embodiment, Z is —NR^(zc)—C(═O)—, wherein C(═O) isbound to T.

In another preferred embodiment, Z is —N═C(S—R^(za))—, wherein T isbound to the carbon atom.

In another preferred embodiment, Z is —NR^(zc)—C(S—R^(za))═, wherein Tis bound to the carbon atom.

In another preferred embodiment, Z is a single bond.

In one preferred embodiment, T is O.

In another preferred embodiment, T is N—R^(T).

In another preferred embodiment, T is N.

In one preferred embodiment, R^(ya) is H, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, which are unsubstituted or substituted with halogen,

phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted orsubstituted with R^(f).

In more preferred embodiment, R^(ya) is H, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, which are unsubstituted or substituted with halogen,

or phenyl which is unsubstituted or substituted with R^(f).

In most preferred embodiment, R^(ya) is H, F, Cl, Br, CH₃, C₂H₅, n-C₃H₇,isopropyl, CH₂F, CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅, CH₂CH₂CF₃,CH₂CF₂CHF₂, CH₂CF₂CF₃, OCH₃, OC₂H₅, n-propyloxy, isopropyloxy, OCH₂F,OCHF₂, OCF₃, OCH₂CF₃, OCF₂CHF₂, OC₂F₅, OCH₂CH₂CF₃, OCH₂CF₂CHF₂,OCH₂CF₂CF₃, or phenyl which is unsubstituted or substituted with R^(f).

In further most preferred embodiment, R^(ya) is H or CH₃;

In one embodiment, R^(yc), R^(zc) are H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,which are unsubstituted or substituted with halogen,

phenyl, or —CH₂-phenyl, wherein the rings are unsubstituted orsubstituted with R^(f).

In more preferred embodiment, R^(yc) and R^(zc) are H, C₁-C₆-alkyl,C₁-C₆-haloalkyl, or phenyl which is unsubstituted or substituted withR^(f).

In most preferred embodiment, R^(yc) and R^(zc) are H, CH₃, C₂H₅,n-C₃H₇, isopropyl, CH₂F, CHF₂, CF₃, CH₂CF₃, CF₂CHF₂, C₂F₅, CH₂CH₂CF₃,CH₂CF₂CHF₂, CH₂CF₂CF₃, or phenyl which is unsubstituted or substitutedwith R^(f).

In further most preferred embodiment, R^(yc) and R^(zc) are H or CH₃;

In one preferred embodiment, R^(T) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, which are unsubstituted orsubstituted with halogen, C(═O)—NR^(b)R^(c), C(═O)—R^(d),SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein thephenyl rings are unsubstituted or substituted with R^(f).

In more preferred embodiment, R^(T) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy, which are unsubstituted orsubstituted with halogen.

In most preferred embodiment, R^(T) is H or C₁-C₆-alkyl.

In another preferred embodiment, R^(zc) together with R^(T) if present,forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in thelinear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety maybe replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moietiesmay be replaced by O or S and/or wherein the linear C₁-C₆-alkylene andthe linear C₂-C₆-alkenylene may be unsubstituted or substituted withR^(h).

In more preferred embodiment, R^(zc) together with R^(T) if present,forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in thelinear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety isreplaced by a carbonyl group.

In another more preferred embodiment, R^(zc) together with R^(T) ifpresent, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂moiety is replaced by a C═N—R′ and wherein 1 or 2 CH₂ moieties may bereplaced by O or S and/or wherein the linear C₁-C₆-alkylene and thelinear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h).

In another more preferred embodiment, R^(zc) together with R^(T) ifpresent, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene 1 or 2 CH₂moieties are replaced by O or S and/or wherein the linear C₁-C₆-alkyleneand the linear C₂-C₆-alkenylene may be unsubstituted or substituted withR^(h).

In one preferred embodiment, R^(za) is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆—C(═O)—R^(d), phenyl, phenylcarbonyl,or —CH₂-phenyl, wherein the phenyl rings are unsubstituted orsubstituted with R^(f);

In more preferred embodiment, R^(za) is H, C₁-C₆-alkyl, orC₁-C₆-haloalkyl;

In most preferred embodiment, R^(za) is H, C₁-C₆-alkyl.

In another preferred embodiment, R^(za) together with R^(T) if present,forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in thelinear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety maybe replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH₂ moietiesmay be replaced by O or S and/or wherein the linear C₁-C₆-alkylene andthe linear C₂-C₆-alkenylene may be unsubstituted or substituted withR^(h);

In more preferred embodiment, R^(za) together with R^(T) if present,forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, where in thelinear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂ moiety isreplaced by a carbonyl group.

In another more preferred embodiment, R^(za) together with R^(T) ifpresent, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂moiety is replaced by a C═N—R′ and wherein 1 or 2 CH₂ moieties may bereplaced by O or S and/or wherein the linear C₁-C₆-alkylene and thelinear C₂-C₆-alkenylene may be unsubstituted or substituted with R^(h).

In another more preferred embodiment, R^(za) together with R^(T) ifpresent, forms C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group, wherein the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene 1 or 2 CH₂moieties are replaced by O or S and/or wherein the linear C₁-C₆-alkyleneand the linear C₂-C₆-alkenylene may be unsubstituted or substituted withR^(h).

In a preferred embodiment, R^(a), R^(b) and R are H, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, which are unsubstituted or substitutedwith halogen,

C₁-C₆-alkylene-CN, phenyl, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f);

In more preferred embodiment, R^(a), R^(b) and R are H, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, which are unsubstituted or substitutedwith halogen,

phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted orsubstituted with R^(f).

In a preferred embodiment, R^(d) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, which are unsubstituted or substituted with halogen,

phenyl, or —CH₂-phenyl, wherein the phenyl rings are unsubstituted orsubstituted with R^(f).

In more preferred embodiment, R^(d) is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,or phenyl which is unsubstituted or substituted with R^(f).

In one preferred embodiment, R^(e) is C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, phenyl, or —CH₂-phenyl, whereinthe phenyl rings are unsubstituted or substituted with R^(f).

In more preferred embodiment, R^(e) is H, C₁-C₆-alkyl, C₁-C₆-haloalkyl,or phenyl unsubstituted or substituted with R^(f).

In one preferred embodiment, R^(f) is halogen, N₃, OH, CN, NO₂, —SCN,—SF, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, which are unsubstituted orsubstituted with halogen,

C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), orS(═O)_(m)R^(e).

In more preferred embodiment, R^(f) is halogen, N₃, OH, CN, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkoxy, which are unsubstituted or substituted with halogen,

C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), orS(═O)_(m)R^(e).

In a preferred embodiment, R^(g) is halogen, N₃, OH, CN, NO₂, —SCN, —SF,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, which are unsubstituted orsubstituted with halogen,

C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c), C(═O)—R^(d),SO₂NR^(b)R^(c), or S(═O)_(m)R^(e).

In more preferred embodiment, R^(g) is halogen, N₃, OH, CN, NO₂,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkoxy, which are unsubstituted or substituted with halogen,

C(═O)—OR^(a), NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c),C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e).

In one embodiment, m is 0.

In another embodiment, m is 1.

In another embodiment, m is 2.

In more preferred embodiment, R¹ are formulas Y-1 to Y-8 wherein

denotes attachment to the 9 membered hetaryl, D is R¹¹ or R¹² andwherein R^(T), R¹¹, R¹², R^(ya), R^(yc), R^(za) and R^(zc) are asdefined in compounds of formula I.

In another more preferred embodiment, R¹ are formulas YZT-1 to YZT-8,wherein

denotes attachment to the 9 membered hetaryl and R¹¹, R¹², R^(T),R^(ya), R^(za) and R^(zc) are as defined in compounds of formula I.

In most preferred embodiment, R¹ are formulas Y-1A to Y-8B, wherein

denotes attachment to the 9 membered hetaryl, D is R¹¹ or R¹².

In one preferred embodiment, R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, which areunsubstituted or substituted with halogen,

aryl, arylcarbonyl, aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl, hetaryl,carbonylhetaryl, C₁-C₄-alkylhetaryl and C₁-C₄-alkyl-hetaryloxy, whereinthe aryl or hetaryl rings are unsubstituted or substituted with R^(g)and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a8-, 9- or 10-membered bicyclic hetaryl.

In more preferred embodiment, R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, which are unsubstituted or substitutedwith halogen,

aryl, arylcarbonyl, aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl, hetaryl,carbonylhetaryl, C₁-C₄-alkylhetaryl and C₁-C₄-alkyl-hetaryloxy, wherethe rings are unsubstituted or substituted with R9 and wherein thehetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or10-membered bicyclic hetaryl.

In most preferred embodiment, R¹¹ is aryl, aryl-C₁-C₄-alkyl, hetaryl, orhetaryl-C₁-C₄-alkyl, wherein the rings are unsubstituted or substitutedwith R9 and where hetaryl in hetaryl or hetaryl-C₁-C₄-alkyl, ispreferably a 5- or 6-membered monocyclic hetaryl such as pyridyl,pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl,thiazolyl, isoxazolyl or isothiazolyl which is unsubstituted orsubstituted with R9.

Examples of particularly preferred radicals R¹¹ are the radicals R¹¹-1to R¹¹-29 summarized in Table A-1 below.

TABLE A-1

R¹¹-1

R¹¹-2

R¹¹-3

R¹¹-4

R¹¹-5

R¹¹-6

R¹¹-7

R¹¹-8

R¹¹-9

R¹¹-10

R¹¹-11

R¹¹-12

R¹¹-13

R¹¹-14

R¹¹-15

R¹¹-16

R¹¹-17

R¹¹-18

R¹¹-19

R¹¹-20

R¹¹-21

R¹¹-22

R¹¹-23

R¹¹-24

R¹¹-25

R¹¹-26

R¹¹-27

R¹¹-28

R¹¹-29

In one embodiment R¹² is a radical of the formula (A¹¹).

wherein # indicates the point of attachment to T and wherein R¹²¹, R¹²²,R¹²³ and R¹²⁴ are as defined above and wherein R¹²¹, R¹²², R¹²³ and R¹²⁴independently of each other and especially in combination preferablyhave the following meanings:

-   -   R¹²¹ is C₁-C₄-alkoxy, in particular OCH₃, OC₂H₅;    -   R¹²² is C₁-C₄-alkoxy, such as OCH₃, OC₂H₅, n-propoxyx or        isopropoxy, or C₃-C₄-alkenyloxy, such as allyloxy, with R¹²² in        particular being OCH₃, OC₂H₅, or n-propoxy;    -   R¹²³ is OH, C₁-C₄-alkoxy, such as OCH₃, OC₂H₅,or        C₃-C₄-alkenyloxy, such as allyloxy, with R¹²³ in particular        being OCH₃, OC₂H₅;    -   R¹²⁴ is C₁-C₄-alkyl, such as CH₃ or C₂H₅, or        C₁-C₄-alkoxy-C₁-C₄-alkyl, such as methoxymethyl, ethoxymethyl,        2-methoxyethyl or 2-ethoxyethyl, with R¹²⁴ in particular being        methyl.

In more preferred embodiment, R¹² is in particular a radical of theformula (A¹¹), e.g. (A¹¹-a) or (A¹¹-b)

wherein # indicates the point of attachment to T and wherein R¹²¹, R¹²²,R¹²³ and R¹²⁴ are as defined above and wherein R¹²¹, R¹²², R¹²³ and R¹²⁴independently of each other and especially in combination preferablyhave the following meanings:

-   -   R¹²¹ is C₁-C₄-alkoxy, in particular OCH₃ or OC₂H₅;    -   R¹²² is C₁-C₄-alkoxy, such as OCH₃, OC₂H₅, n-propoxyx or        isopropoxy, or C₃-C₄-alkenyloxy, such as allyloxy, with R¹²² in        particular being OCH₃, OC₂H₅ or n-propoxy;    -   R¹²³ is OH, C₁-C₄-alkoxy, such as OCH₃ or OC₂H₅, or        C₃-C₄-alkenyloxy, such as allyloxy, with R¹²³ in particular        being OCH₃ or OC₂H₅;    -   R¹²⁴ is C₁-C₄-alkyl, such as CH₃ or C₂H₅, or        C₁-C₄-alkoxy-C₁-C₄-alkyl, such as methoxymethyl, ethoxymethyl,        2-methoxyethyl or 2-ethoxyethyl, with R¹²⁴ in particular being        methyl.

Particular examples of radicals R¹² are the following radicals A¹¹-1,A¹¹-1a, A¹¹-1b, A¹¹-2, A¹¹-2a, A¹¹-2b, A¹¹-3, A¹¹-3a and A¹¹-3b:

In a more preferred embodiment compounds of formula I are selected fromcompounds of formula I.A to I.V.

wherein, Ar is phenyl or 5- or 6-membered hetaryl ring which issubstituted with R^(Ar);

R^(Ar) is halogen, OH, CN, NO₂, SCN, C₁-C₆-alkyl, C₁-C₆-alkoxy, orS—R^(e), wherein the alkyl and alkoxy are unsubstituted or substitutedwith halogen;

R² is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂—C-alkynyl,C₁-C₄-alkyl-C₁-C₆-alkoxy, or C₃-C₆-cycloalkyl, which are unsubstitutedor substituted with halogen, and phenyl which is unsubstituted orsubstituted with R^(f);

Q is —N═C(X)—, —N(R²)—C(═NR)—, or —N(R²)—C(═S)—; wherein Ar is bound toeither side of Q;

R^(A) is H, halogen, OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, or C₂-C₆-alkenyl;

R^(B) is H, halogen, OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, or C₂-C₆-alkenyl;

R^(B1) is H, halogen, OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, or C₂-C₆-alkenyl;

and R¹ is Y—Z-T-R¹¹ or Y—Z-T-R¹², as defined in formula I.

preferred compounds of formula I are the compounds of formula I.1 toI.6,

more preferred compounds of formula I are compounds of formula I.1 toI.6, wherein R¹ is selected from Y-1A, Y-1B, Y-2A, Y-2B3, Y-3A, Y-3B3,Y-3C, Y-31D, Y-4A, Y-4B3, Y-4C, Y-41D, Y-5A, Y-5B3, Y-6A, Y-6B3, Y-7A,Y-7B3, Y-8A, and Y-8B3; wherein D is R¹¹ or R¹², and other variables areas defined herein.

most preferred compounds of formula I are compounds of formula I.1, I.3,I.4, or I.5, wherein

X is H;

R is H, C₁-C₆-alkyl, or C₁-C₆-alkoxy;

R² is H or C₁-C₆-alkyl;

Ar is Ar¹, Ar², Ar³, or Ar¹⁴;

A¹ is CH;

A² is CH;

A³ is N or CH;

W is N or S;

R¹ is Y-1A, Y-3C, Y-3D, Y-5A, Y-6A, Y-7A or Y-8A; wherein D is R¹¹ orR¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is (A¹¹-1) or (A¹¹-3), preferably (A¹¹-1a) or (A¹¹-3a).

most preferred compounds of formula I are compounds of formula I.1 toI.6, wherein

X is H, CH₃, CN, F, OCH₃, NHCH₃, CH═NOCH₃, SCH₃, 2-OCF₃-phenyl, or2-OCF₃-benzyl;

R is H, CH₃, OCH₃, NHCH₃, or SCH₃;

R² is H, CH₃, C₂H₅, or CH₂COOC₂H₅;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷, Ar⁸, Ar⁹, Ar¹⁰, Ar¹¹, Ar¹²,Ar¹³, or Ar¹⁴;

A¹ is N, CH, or CH₃;

A² is N, CH, or CH₃;

A³ is N, CH, or CH₃;

W is N, O, or S;

R¹ is Y-1A, Y-1B, Y-2A, Y-2B3, Y-3A, Y-3B3, Y-3C, Y-31D, Y-4A, Y-4B3,Y-4C, Y-41D, Y-5A, Y-5B3, Y-6A, Y-61, Y-7A, Y-73, Y-8A, or Y-87; whereinD is R¹¹ or R¹²;

R¹¹ is R¹¹-1, R¹¹-2, R¹¹-3, R¹¹-5, R¹¹-6, R¹¹-7, R¹¹-8, R¹¹-9, R¹¹-10,R¹¹-11, R¹¹-12, R¹¹-13, R¹¹-14, R¹¹-15, R¹¹-16, R¹¹-17, R¹¹-18, R¹¹-19,R¹¹-20, R¹¹-21, R¹¹-22, R¹¹-23, R¹¹-25, R¹¹- 26, R¹¹-27, R¹¹-28, orR¹¹-29;

R¹² is (A¹¹-1), (A¹¹-2), or (A¹¹-3).

most preferred compounds of formula I are compounds of formula I.1 toI.6, wherein

X is H, CH₃, CN, F, OCH₃, NHCH₃, CH═NOCH₃, SCH₃, 2-OCF₃-phenyl, or2-OCF₃-benzyl;

R is H, CH₃, OCH₃, NHCH₃, or SCH₃;

R² is H, CH₃, C₂H₅, or CH₂COOC₂H₅;

Ar is Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷, Ar⁸, Ar⁹, Ar¹⁰, Ar¹¹, or Ar¹²;

A¹ is N, CH, or CH₃;

A² is N, CH, or CH₃;

A³ is N, CH, or CH₃;

W is N, O, or S;

R¹ is Y-1A, Y-1B, Y-2A, Y-2B, Y-3A, Y-3B, Y-3C, Y-3D, Y-4A, Y-4B, Y-4C,Y-4D, Y-5A, Y-5B, Y-6A, Y-6B, Y-7A, Y-7B, Y-8A, or Y-8B; wherein D isR¹¹ or R¹²;

R¹¹ is R¹¹-1, R¹¹-2, R¹¹-3, R¹¹-5, R¹¹-6, R¹¹-7, R¹¹-8, R¹¹-9, R¹¹-10,R¹¹-11, R¹¹-12, R¹¹-13, R¹¹-14, R¹¹-15, R¹¹-16, R¹¹-17, R¹¹-18, R¹¹-19,R¹¹-20, R¹¹-21, R¹¹-22, R¹¹-23, R¹¹-25, R¹¹- 26, R¹¹-27, R¹¹-28, orR¹¹-29;

R¹² is (A¹¹-1), (A¹¹-2), or (A¹¹-3).

Most particularly preferred compounds of formula I are compounds offormula I.1, I.3, I.4, or I.5, wherein

X is H;

R is H, C₁-C₆-alkyl, or C₁-C₆-alkoxy;

R² is H or C₁-C₆-alkyl;

Ar is Ar¹, Ar², Ar³, or Ar¹⁴;

A¹ is CH;

A² is CH;

A³ is N or CH;

W is N or S;

R¹ is Y-1A, Y-3C, Y-3D, Y-5A, Y-6A, Y-7A, or Y-8A; wherein D is R¹¹ orR¹²;

R¹¹ is R¹¹-1 or R¹¹-10;

R¹² is (A¹¹-1) or (A¹¹-3), preferably (A¹¹-1a) or (A¹¹-3a).

As used herein, the term “compound(s) of the present invention” or“compound(s) according to the invention” refers to the compound(s) offormula (I) as defined above, which are also referred to as “compound(s)of formula I” or “compound(s) I” or “formula I compound(s)”, andincludes their salts, tautomers, stereoisomers, and N-oxides.

The present invention also relates to a mixture of at least one compoundof the present invention with at least one mixing partner as definedherein after. Preferred are binary mixtures of one compound of thepresent invention as component I with one mixing partner as definedherein after as component II. Preferred weight ratios for such binarymixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1:1000,more preferably from 100:1 to 1:100, particularly preferably from 10:1to 1:10. In such binary mixtures, components I and II may be used inequal amounts, or an excess of component I, or an excess of component IImay be used.

Mixing partners can be selected from pesticides, in particularinsecticides, nematicides, and acaricides, fungicides, herbicides, plantgrowth regulators, fertilizers, and the like. Preferred mixing partnersare insecticides, nematicides and fungicides.

The following list M of pesticides, grouped and numbered according theMode of Action Classification of the Insecticide Resistance ActionCommittee (IRAC), together with which the compounds of the presentinvention can be used and with which potential synergistic effects mightbe produced, is intended to illustrate the possible combinations, butnot to impose any limitation:

M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1Acarbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; orfrom the class of M.1B organophosphates, for example acephate,azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;

M.2. GABA-gated chloride channel antagonists such as: M.2A cyclodieneorganochlorine compounds, as for example endosulfan or chlordane; orM.2B fiproles (phenyl-pyrazoles), as for example ethiprole, fipronil,flufiprole, pyrafluprole and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, forexample acrinathrin, allethrin, d-cis—trans allethrin, d-transallethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambdacyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, thetacypermethrin, zeta-cypermethrin, cyphenothrin,deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox,heptafluthrin, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin,permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum),resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin,tralomethrin and transfluthrin; or M.3B sodium channel modulators suchas DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class ofM.4A neonicotinoids, for example acetamiprid, clothianidin, cycloxaprid,dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; orthe compounds M.4A.2:(2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide;or M4.A.3:1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine;or from the class M.4B nicotine;

M.5 Nicotinic acetylcholine receptor allosteric activators from theclass of spinosyns,

for example spinosad or spinetoram;

M.6 Chloride channel activators from the class of avermectins andmilbemycins, for example abamectin, emamectin benzoate, ivermectin,lepimectin or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues ashydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb orM.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, for example M.8Aalkyl halides as methyl bromide and other alkyl halides, or M.8Bchloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartaremetic;

M.9 Selective homopteran feeding blockers, for example M.9B pymetrozine,or M.9C flonicamid;

M.10 Mite growth inhibitors, for example M.10A clofentezine, hexythiazoxand diflovidazin, or M.10B etoxazole;

M.11 Microbial disruptors of insect midgut membranes, for exampleBacillus thuringiensis or Bacillus sphaericus and the insecticdalproteins they produce such as Bacillus thuringiensis subsp. israelensis,Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki and Bacillus thuringiensis subsp.tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab,mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;

M.12 Inhibitors of mitochondrial ATP synthase, for example M.12Adiafenthiuron, or M.12B organotin miticides such as azocyclotin,cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, forexample nereistoxin analogues as bensultap, cartap hydrochloride,thiocyclam or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureasas for example bistrifluron, chlorfluazuron, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1, as for examplebuprofezin;

M.17 Moulting disruptors, Dipteran, as for example cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, for examplemethoxyfenozide, tebufenozide, halofenozide, fufenozide orchromafenozide;

M.19 Octopamin receptor agonists, as for example amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, forexample M.20A hydramethylnon, or M.20B acequinocyl, or M.20Cfluacrypyrim;

M.21 Mitochondrial complex I electron transport inhibitors, for exampleM.21A METI acaricides and insecticides such as fenazaquin,fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, orM.21B rotenone;

M.22 Voltage-dependent sodium channel blockers, for example M.22Aindoxacarb, or M.22B metaflumizone, or M.22B.1:2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamideor M.22B.2:N-(3-Chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;

M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic andTetramic acid derivatives, for example spirodiclofen, spiromesifen orspirotetramat;

M.24 Mitochondrial complex IV electron transport inhibitors, for exampleM.24A phosphine such as aluminium phosphide, calcium phosphide,phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such asbeta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, as forexample flubendiamide, chlorantraniliprole (Rynaxypyr®),cyantraniliprole (Cyazypyr®), tetraniliprole, or the phthalamidecompounds M.28.1:(R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamidand M.28.2:(S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,or the compound M.28.3:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide(proposed ISO name: cyclaniliprole), or the compound M.28.4:methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;or a compound selected from M.28.5a) to M.28.5d) and M.28.5h) toM.28.5l): M.28.5a)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5b)N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5c)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5d)N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5h)N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5i)N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide;M.28.5j)3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide;M.28.5k)3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide;M.28.5l)N-[4-Chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide;or

M.28.6: cyhalodiamide; or;

M.29. insecticidal active compounds of unknown or uncertain mode ofaction, as for example afidopyropen, afoxolaner, azadirachtin,amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate,chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim,flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone,fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl,pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or thecompounds

M.29.3:11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,or the compound

M.29.4:3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,or the compound

M.29.5:1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,or actives on basis of Bacillus firmus (Votivo, 1-1582); or

a compound selected from the of M.29.6, wherein the compound M.29.6a) toM.29.6k): M.29.6a)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6b)(E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6c)(E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;M.29.6d)(E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6e)(E/Z)-N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6f)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;M.29.6g)(E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;M.29.6h)(E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6i)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoropropanamide.);M.29.6j)N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluorothioacetamide;or M.29.6k)N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N′-isopropyl-acetamidine;or the compounds

M.29.8: fluazaindolizine; or the compounds

M.29.9.a):4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide;or M.29.9.b): fluxametamide; or

M.29.10:5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;or a compound selected from the of M.29.11, wherein the compoundM.29.11b) to M.29.11p): M.29.11.b)3-(benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide;M.29.11.c)3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide;M.29.11.d)N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;M.29.11.e)N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;M.29.11.f)4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;M.29.11.g)3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;M.29.11.h)2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide;M.29.11.i)4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;M.29.11.j)4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide;M.29.11.k)N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;M.29.11.l)N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;M.29.11.m)N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;M.29.11.n)4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;M.29.11.o)4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;M.29.11.p)N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;or

a compound selected from the of M.29.12, wherein the compound M.29.12a)to M.29.12m): M.29.12.a)2-(1,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.29.12.b)2-[6-[2-(5-Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;M.29.12.c) 2-[6-[2-(3-Pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;M.29.12.d)N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;M.29.12.e)N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;M.29.12.f)N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12.g)N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12.h)N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12.i)N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12.j)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide;M.29.12.k)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide;M.29.12.l)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide;M.29.12.m)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide;or the compounds

M.29.14a)1-[(6-Chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitroimidazo[1,2-a]pyridine;or M.29.14b)1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol;or the compounds

M.29.16a)1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; orM.29.16b)1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16c)N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide;M.29.16d)1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16e)N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16f)1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16g)1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16h)N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16i)1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;or M.29.16j)1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide,or

M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j):M.29.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide;M.29.17b) N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;M.29.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;M.29.17d)2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide;M.29.17e)2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide;M.29.17f) methyl2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate;M.29.17g)N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide;M.29.17h)N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide;M.29.17i)2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide;M.29.17j)N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,or

M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d):M.29.18a)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide;M.29.18b)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide;M.29.18c)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide;M.29.18d)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;or the compound

M.29.19 sarolaner, or the compound

M.29.20 lotilaner.

The commercially available compounds of the M listed above may be foundin The Pesticide Manual, 16th Edition, C. MacBean, British CropProtection Council (2013) among other publications. The online PesticideManual is updated regularly and is accessible throughhttp://bcpcdata.com/pesticide-manual.html.

Another online data base for pesticides providing the ISO common namesis http://www.alanwood.net/pesticides.

The M.4 neonicotinoid cycloxaprid is known from WO2010/069266 andWO2011/069456, the neonicotinoid M.4A.2, sometimes also to be named asguadipyr, is known from WO2013/003977, and the neonicotinoid M.4A.3(approved as paichongding in China) is known from WO2007/101369. Themetaflumizone analogue M.22B.1 is described in CN10171577 and theanalogue M.22B.2 in CN102126994. The phthalamides M.28.1 and M.28.2 areboth known from WO2007/101540. The anthranilamide M.28.3 is described inWO2005/077934. The hydrazide compound M.28.4 is described inWO2007/043677. The anthranilamides M.28.5a) to M.28.5d) and M.28.5h) aredescribed in WO 2007/006670, WO2013/024009 and WO2013/024010, theanthranilamide M.28.5i) is described in WO2011/085575, M.28.5j) inWO2008/134969, M.28.5k) in US2011/046186 and M.28.5l) in WO2012/034403.The diamide compound M.28.6 can be found in WO2012/034472. Thespiroketal-substituted cyclic ketoenol derivative M.29.3 is known fromWO2006/089633 and the biphenyl-substituted spirocyclic ketoenolderivative M.29.4 from WO2008/067911. The triazoylphenylsulfide M.29.5is described in WO2006/043635, and biological control agents on thebasis of Bacillus firmus are described in WO2009/124707. The compoundsM.29.6a) to M.29.6i) listed under M.29.6 are described in WO2012/029672,and M.29.6j) and M.29.6k) in WO2013/129688. The nematicide M.29.8 isknown from WO2013/055584. The isoxazoline M.29.9.a) is described inWO2013/050317. The isoxazoline M.29.9.b) is described in WO2014/126208.The pyridalyl-type analogue M.29.10 is known from WO2010/060379. Thecarboxamides broflanilide and M.29.11.b) to M.29.11.h) are described inWO2010/018714, and the carboxamides M.29.11i) to M.29.11.p) inWO2010/127926. The pyridylthiazoles M.29.12.a) to M.29.12.c) are knownfrom WO2010/006713, M.29.12.d) and M.29.12.e) are known fromWO2012/000896, and M.29.12.f) to M.29.12.m) from WO2010/129497. Thecompounds M.29.14a) and M.29.14b) are known from WO2007/101369. Thepyrazoles M.29.16.a) to M.29.16h) are described in WO2010/034737,WO2012/084670, and WO2012/143317, respectively, and the pyrazolesM.29.16i) and M.29.16j) are described in U.S. 61/891,437. Thepyridinylindazoles M.29.17a) to M.29.17.j) are described inWO2015/038503. The pyridyl-pyrazoles M.29.18a) to M.29.18d) aredescribed in US2014/0213448. The isoxazoline M.29.19 is described inWO2014/036056. The isoxazoline M.29.20 is known from WO2014/090918.

The following list of fungicides, in conjunction with which thecompounds of the present invention can be used, is intended toillustrate the possible combinations but does not limit them:

A) Respiration Inhibitors

-   -   Inhibitors of complex III at Q_(o) site (e. g. strobilurins):        azoxystrobin (A.1.1), coumethoxy-strobin (A.1.2), coumoxystrobin        (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5),        fenamin-strobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7),        fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin        (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12),        picoxy.strobin (A.1.13), pyraclostrobin (A.1.14),        pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16),        trifloxystrobin (A.1.17),        2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide        (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb        (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21),        methyl-N-[2-[(1,4-dimethyl-5-phenylpyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate        (A.1.22),        1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.23),        1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.24),        1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one        (A.1.25),        1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one        (A.1.26),        1-[2-[[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one        (A.1.27),        1-[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one        (A.1.28),        1-[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.29),        1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.30),        1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.31),        1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one        (A.1.32),        1-methyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one        (A.1.33),        (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.34),        (Z,2E)-5-[1-(4-chorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide        (A.1.35),        (Z,2E)-5-[1-(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.36),    -   inhibitors of complex III at Q_(i) site: cyazofamid (A.2.1),        amisulbrom (A.2.2),        [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.3),        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxypyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.4),        [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.5),        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.6);        (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl        2-methylpropanoate (A.2.7),        (3S,6S,7R,8R)-8-benzyl-3-[3-[(isobutyryloxy)methoxy]-4-methoxypicolinamido]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl        isobutyrate (A.2.8);    -   inhibitors of complex II (e. g. carboxamides): benodanil        (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid        (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7),        flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10),        isofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13),        oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15),        sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18),        N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide        (A.3.19),        N-(2-(1,3,3-trimethyl-butyl)phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide        (A.3.20),        3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.21),        3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.22),        1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.23),        3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.24),        1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.25),        N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1,3-dimethyl-pyrazole-4-carboxamide        (A.3.26),        N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide        (A.3.27);    -   other respiration inhibitors (e. g. complex I, uncouplers):        diflumetorim (A.4.1),        (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine        (A.4.2); nitrophenyl derivates: binapacryl (A.4.3), dinobuton        (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7);        organometal compounds: fentin salts, such as fentin-acetate        (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10);        ametoctradin (A.4.11); and silthiofam (A.4.12);

B) Sterol Biosynthesis Inhibitors (SBI Fungicides)

-   -   C14 demethylase inhibitors (DMI fungicides): triazoles:        azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3),        cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole        (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8),        fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole        (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13),        imibenconazole (B.1.14), ipconazole (B.1.15), metconazole        (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19),        paclo-butrazole (B.1.20), penconazole (B.1.21), propiconazole        (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24),        tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon        (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29),        uniconazole (B.1.30),        1-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazolo        (B.1.31),        2-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol        (B.1.32),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol        (B.1.33),        1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol        (B.1.34),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.35),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.36),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.37),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol        (B.1.38),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.39),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol        (B.1.40),        2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol        (B.1.41),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol        (B.1.51); imidazoles: imazalil (B.1.42), pefurazoate (B.1.43),        prochloraz (B.1.44), triflumizol (B.1.45); pyrimidines,        pyridines and piperazines: fenarimol (B.1.46), nuarimol        (B.1.47), pyrifenox (B.1.48), triforine (B.1.49),        [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol        (B.1.50);    -   Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph        (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4),        tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7),        spiroxamine (B.2.8);    -   Inhibitors of 3-keto reductase: fenhexamid (B.3.1);

C) Nucleic Acid Synthesis Inhibitors

-   -   phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1),        benalaxyl-M (C.1.2), kiral-axyl (C.1.3), metalaxyl (C.1.4),        metalaxyl-M (mefenoxam, C.1.5), ofurace (C.1.6), oxadixyl        (C.1.7);    -   others: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid        (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5),        5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),        5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7);

D) Inhibitors of Cell Division and Cytoskeleton

-   -   tubulin inhibitors, such as benzimidazoles, thiophanates:        benomyl (D1.1), carbendazim (D1.2), fuberidazole (D1.3),        thiabendazole (D1.4), thiophanate-methyl (D1.5);        triazolopyrimidines:        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine        (D1.6);    -   other cell division inhibitors: diethofencarb (D2.1), ethaboxam        (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5),        metrafenone (D2.6), pyriofenone (D2.7);

E) Inhibitors of Amino Acid and Protein Synthesis

-   -   methionine synthesis inhibitors (anilino-pyrimidines):        cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);    -   protein synthesis inhibitors: blasticidin-S(E.2.1), kasugamycin        (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin        (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine        (E.2.7), validamycin A (E.2.8);

F) Signal Transduction Inhibitors

-   -   MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione        (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fenpiclonil        (F.1.5), fludioxonil (F.1.6);    -   G protein inhibitors: quinoxyfen (F.2.1);

G) Lipid and Membrane Synthesis Inhibitors

-   -   Phospholipid biosynthesis inhibitors: edifenphos (G.1.1),        iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);    -   lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2),        tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5),        chloroneb (G.2.6), etridiazole (G.2.7);    -   phospholipid biosynthesis and cell wall deposition: dimethomorph        (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph        (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6),        valifenalate (G.3.7) and        N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic        acid-(4-fluorophenyl) ester (G.3.8);    -   compounds affecting cell membrane permeability and fatty acides:        propamocarb (G.4.1);    -   fatty acid amide hydrolase inhibitors: oxathiapiprolin (G.5.1),        2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl        methanesulfonate (G.5.2),        2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)        1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl        methanesulfonate (G.5.3);

H) Inhibitors with Multi Site Action

-   -   inorganic active substances: Bordeaux mixture (H.1.1), copper        acetate (H.1.2), copper hydroxide (H.1.3), copper oxychloride        (H.1.4), basic copper sulfate (H.1.5), sulfur (H.1.6);    -   thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2),        maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6),        thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);    -   organochlorine compounds (e. g. phthalimides, sulfamides,        chloronitriles): anilazine (H.3.1), chlorothalonil (H.3.2),        captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid        (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8),        pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10),        tolylfluanid (H.3.11),        N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methylbenzenesulfonamide        (H.3.12);    -   guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine        free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5),        iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7),        iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9),        2,6-dimethyl-1H,5H[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone        (H.4.10);

I) Cell Wall Synthesis Inhibitors

-   -   inhibitors of glucan synthesis: validamycin (I.1.1), polyoxin B        (I.1.2);    -   melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole        (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil        (I.2.5);

J) Plant Defence Inducers

-   -   acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil        (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5);        phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7),        phosphorous acid and its salts (J.1.8), potassium or sodium        bicarbonate (J.1.9);

K) Unknown Mode of Action

-   -   bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3),        cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6),        diclomezine (K.1.7), difenzoquat (K.1.8),        difenzoquat-methylsulfate (K.1.9), diphenylamin (K.1.10),        fenpyrazamine (K.1.11), flumetover (K.1.12), flusulfamide        (K.1.13), flutianil (K.1.14), methasulfocarb (K.1.15),        nitrapyrin (K.1.16), nitrothal-isopropyl (K.1.18),        oxathiapiprolin (K.1.19), tolprocarb (K.1.20), oxin-copper        (K.1.21), proquinazid (K.1.22), tebufloquin (K.1.23),        tecloftalam (K.1.24), triazoxide (K.1.25),        2-butoxy-6-iodo-3-propylchromen-4-one (K.1.26),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone        (K.1.27),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone        (K.1.28),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone        (K.1.29),        N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl        acetamide (K.1.30),        N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.31),        N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.32),        N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsianyl-propoxy)phenyl)-N-ethyl-N-methyl        formamidine (K.1.33),        N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine (K.1.34), methoxy-acetic acid        6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester (K.1.35),        3-[5-(4-methylphenyl)-2,3-dimethylisoxazolidin-3-yl]-pyridine        (K.1.36),        3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine        (pyrisoxazole) (K.1.37), N-(6-methoxy-pyridin-3-yl)        cyclopropanecarboxylic acid amide (K.1.38),        5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole        (K.1.39),        2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide,        ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40),        picarbutrazox (K.1.41), pentyl        N-[6-[[(Z)[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate        (K.1.42),        2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol        (K.1.43),        2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol        (K.1.44),        3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline        (K.1.45),        3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline        (K.1.46),        3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline        (K.1.47),        9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine        (K.1.48).

The fungicides described by common names, their preparation and theiractivity e.g. against harmful fungi is known (cf.:http://www.alanwood.net/pesticides/); these substances are commerciallyavailable.

The fungicides described by IUPAC nomenclature, their preparation andtheir pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6),587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970;EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE10021412; DE 102005009458; U.S. Pat. Nos. 3,296,272; 3,325,503; WO98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO07/82098; WO 07/90624, WO 11/028657, WO2012/168188, WO 2007/006670, WO2011/77514; WO13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO13/024010 and WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833).

Biopesticides

Suitable mixing partners for the compounds of the present invention alsoinclude biopesticides.

Biopesticides have been defined as a form of pesticides based onmicro-organisms (bacteria, fungi, viruses, nematodes, etc.) or naturalproducts (compounds, such as metabolites, proteins, or extracts frombiological or other natural sources) (U.S. Environmental ProtectionAgency: http://www.epa.gov/pesticides/biopesticides/). Biopesticidesfall into two major classes, microbial and biochemical pesticides:

(1) Microbial pesticides consist of bacteria, fungi or viruses (andoften include the metabolites that bacteria and fungi produce).Entomopathogenic nematodes are also classified as microbial pesticides,even though they are multi-cellular.

(2) Biochemical pesticides are naturally occurring substances or orstructurally-similar and functionally identical to a naturally-occurringsubstance and extracts from biological sources that control pests orprovide other crop protection uses as defined below, but have non-toxicmode of actions (such as growth or developmental regulation,attractents, repellents or defence activators (e.g. induced resistance)and are relatively non-toxic to mammals.

Biopesticides for use against crop diseases have already establishedthemselves on a variety of crops. For example, biopesticides alreadyplay an important role in controlling downy mildew diseases. Theirbenefits include: a 0-Day Pre-Harvest Interval, the ability to use undermoderate to severe disease pressure, and the ability to use in mixtureor in a rotational program with other registered pesticides.

A major growth area for biopesticides is in the area of seed treatmentsand soil amendments. Biopesticidal seed treatments are e.g. used tocontrol soil borne fungal pathogens that cause seed rots, damping-off,root rot and seedling blights. They can also be used to control internalseed borne fungal pathogens as well as fungal pathogens that are on thesurface of the seed. Many biopesticidal products also show capacities tostimulate plant host defenses and other physiological processes that canmake treated crops more resistant to a variety of biotic and abioticstresses or can regulate plant growth. Many biopesticidal products alsoshow capacities to stimulate plant health, plant growth and/or yieldenhancing activity.

The following list of biopesticides, in conjunction with which thecompounds of the present invention can be used, is intended toillustrate the possible combinations but does not limit them:

L) Biopesticides

L1) Microbial pesticides with fungicidal, bactericidal, viricidal and/orplant defense activator activity: Ampelomyces quisqualis, Aspergillusflavus, Aureobasidium pullulans, Bacillus altitudinis, B.amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B.pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var.amyloliquefaciens, Candida oleophila, C. saitoana, Clavibactermichiganensis (bacteriophages), Coniothyrium minitans, Cryphonectriaparasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusariumoxysporum, Clonostachys rosea f. catenulate (also named Gliocladiumcatenulatum), Gliocladium roseum, Lysobacter antibioticus, L.enzymogenes, Metschnikowia fructicola, Microdochium dimerum,Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei,Paenibacillus polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsisgigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozymaflocculosa, Pichia anomala, Pythium oligandrum, Sphaerodesmycoparasitica, Streptomyces griseoviridis, S. lydicus, S.violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T.asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T.harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhulaphacorrhiza, Ulocladium oudemansi, Verticillium dahlia, zucchini yellowmosaic virus (avirulent strain);

L2) Biochemical pesticides with fungicidal, bactericidal, viricidaland/or plant defense activator activity: harpin protein, Reynoutriasachalinensis extract;

L3) Microbial pesticides with insecticidal, acaricidal, molluscidaland/or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus,B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp.israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp.tenebrionis, Beauveria bassiana, B. brongniartii, Burkholderia spp.,Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV),Cryptophlebia leucotreta granulovirus (CrIeGV), Flavobacterium spp.,Heicoverpa armigera nucleopolyhedrovirus (HearNPV), Heicoverpa zeanucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsidnucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isariafumosorosea, Lecanicillium longisporum, L. muscarium, Metarhiziumanisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var.acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus,Paenibacillus popilliae, Pasteurla spp., P. nishizawae, P. penetrans, P.ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodopteralittoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S.feltiae, S. kraussei, Streptomycesgalbus, S. microflavus;

L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal,pheromone and/or nematicidal activity: L-carvone, citral,(E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyldecadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptylbutyrate, isopropyl myristate, lavanulyl senecioate, cis—jasmone,2-methyl 1-butanol, methyl eugenol, methyl jasmonate,(E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate,(E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol, pentatermanone,(E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-ylacetate, Z-7-tetradecen-2-one, Z-9-tetradecen-1-yl acetate,Z-11-tetradecenal, Z-11-tetradecen-1-ol, extract of Chenopodiumambrosiodes, Neem oil, Quillay extract;

L5) Microbial pesticides with plant stress reducing, plant growthregulator, plant growth promoting and/or yield enhancing activity:Azospirillum amazonense, A. brasillense, A. lipoferum, A. irakense, A.halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B.liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices,Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. l. bv.trifolii, R. l. bv. viciae, R. tropici, Sinorhizobium meliloti.

The biopesticides from L1) and/or L2) may also have insecticidal,acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing,plant growth regulator, plant growth promoting and/or yield enhancingactivity. The biopesticides from L3) and/or L4) may also havefungicidal, bactericidal, viricidal, plant defense activator, plantstress reducing, plant growth regulator, plant growth promoting and/oryield enhancing activity. The biopesticides from L5) may also havefungicidal, bactericidal, viricidal, plant defense activator,insecticidal, acaricidal, molluscidal, pheromone and/or nematicidalactivity.

Many of these biopesticides have been deposited under deposition numbersmentioned herein (the prefices such as ATCC or DSM refer to the acronymof the respective culture collection, for details see e. g. here:http://www.wfcc.info/ccinfo/collection/by_acronym/), are referred to inliterature, registered and/or are commercially available: mixtures ofAureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 inKonstanz, Germany (e. g. blastospores in BlossomProtect® from bio-fermGmbH, Austria), Azospirillum brasilense Sp245 originally isolated inwheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR11005; e. g. GEL-FIX® Gramineas from BASF Agricultural Specialties Ltd.,Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e. g. in AzoMax fromNovozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazilor Simbiose-Maz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425,2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 andB-50331; U.S. Pat. No. 8,445,255); B. amyloliquefaciens spp. plantarumD747 isolated from air in Kikugawa-shi, Japan (US 20130236522 A1; FERMBP-8234; e. g. Double Nickel™ 55 WDG from Certis LLC, USA), B.amyloliquefaciens spp. plantarum FZB24 isolated from soil inBrandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot.105, 181-197, 1998; e. g. Taegr® from Novozyme Biologicals, Inc., USA),B. amyloliquefaciens ssp. plantarum FZB42 isolated from soil inBrandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998;e. g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. amyloliquefaciensssp. plantarum MB1600 isolated from faba bean in Sutton Bonington,Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRLB-50595; US 2012/0149571 A1; e. g. Integral® from BASF Corp., USA), B.amyloliquefaciens spp. plantarum QST-713 isolated from peach orchard in1995 in California, U.S.A. (NRRL B-21661; e. g. Serenade® MAX from BayerCrop Science LP, USA), B. amyloliquefaciens spp. plantarum TJ1000isolated in 1992 in South Dakoda, U.S.A. (also called 1BE; ATCC BAA-390;CA 2471555 A1; e. g. QuickRoots™ from TJ Technologies, Watertown, S.Dak., USA), B. firmus CNCM I-1582, a variant of parental strain EIP-N1(CNCM I-1556) isolated from soil of central plain area of Israel (WO2009/126473, U.S. Pat. No. 6,406,690; e. g. Votivo® from BayerCropScience LP, USA), B. pumilus GHA 180 isolated from apple treerhizosphere in Mexico (IDAC 260707-01; e. g. PRO-MIX® BX from PremierHorticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to asBU-F22 and BU-F33 isolated at least before 1993 from cucumber infestedby Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; U.S. Pat. No.8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses inSouth Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e. g.BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., SouthAfrica), B. pumilus QST 2808 was isolated from soil collected inPohnpei, Federated States of Micronesia, in 1998 (NRRL B-30087; e. g.Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU288 (NRRL B-50304; U.S. Pat. No. 8,445,255), B. subtils FB17 also calledUD 1022 or UD10-22 isolated from red beet roots in North America (ATCCPTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010/0260735;WO 2011/109395); B. thuringiensis ssp. aizawai ABTS-1857 isolated fromsoil taken from a lawn in Ephraim, Wis., U.S.A., in 1987 (also calledABG-6346; ATCC SD-1372; e. g. XenTari® from BioFa AG, Münsingen,Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1 isolated in1967 from diseased Pink Bollworm black larvae in Brownsville, Tex.,U.S.A. (ATCC SD-1275; e. g. Dipel® DF from Valent BioSciences, IL, USA),B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers(NRRL B-50753; e. g. Beta Pro® from BASF Agricultural Specialities (Pty)Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1, a mutant of strainNB-125, a wild type strain isolated in 1982 from a dead pupa of thebeetle Tenebrio molitor (DSM 5480; EP 585 215 B1; e. g. Novodor® fromValent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1(ATCC 74040; e. g. Naturalis from CBC (Europe) S.r.l., Italy), B.bassiana PPRI 5339 isolated from the larva of the tortoise beetleConchyloctenia punctata (NRRL 50757; e. g. BroadBand® from BASFAgricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobiumelkanii strains SEMIA 5019 (also called 29W) isolated in Rio de Janeiro,Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul,from an area previously inoculated with a North American isolate, andused in commercial inoculants since 1968 (Appl. Environ. Microbiol.73(8), 2635, 2007; e. g. GELFIX 5 from BASF Agricultural SpecialtiesLtd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A.(Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e. g. inRhizoflo®, Histick, Hicoat Super from BASF Agricultural SpecialtiesLtd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109,SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47,81-89, 2011); B. japonicum strains deposited at SEMIA known from Appl.Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil inCerrados region, Brazil by Embrapa-Cerrados used in commercialinoculants since 1992 (CPAC 15; e. g. GELFIX 5 or ADHERE 60 from BASFAgricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtainedunder lab conditions by Embrapa-Cerrados in Brazil and used incommercial inoculants since 1992, being a natural variant of SEMIA 586(CB1809) originally isolated in U.S.A. (CPAC 7; e. g. GELFIX 5 or ADHERE60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp.A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO2013/032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitansCON/M/91-08 isolated from oilseed rape (WO 1996/021358; DSM 9660; e. g.Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin(alpha-beta) protein (Science 257, 85-88, 1992; e. g. Messenger™ orHARP-N-Tek from Plant Health Care plc, U.K.), Helcoverpa armigeranucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 112-126,2011; e. g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata®from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland,Australia), Helcoverpa zea single capsid nucleopolyhedrovirus (HzSNPV)(e. g. Gemstar® from Certis LLC, USA), Helicoverpa zeanucleopolyhedrovirus ABA-NPV-U (e. g. Heligen® from AgBiTech Pty Ltd.,Queensland, Australia), Heterorhabditis bacteriophora (e. g. Nemasys® Gfrom BASF Agricultural Specialities Limited, UK), Isaria fumosoroseaApopka-97 isolated from mealy bug on gynura in Apopka, Fla., U.S.A.(ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e. g.PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var.anisopliae F₅₂ also called 275 or V275 isolated from codling moth inAustria (DSM 3884, ATCC 90448; e. g. Met52® Novozymes Biologicals BioAgGroup, Canada), Metschnikowia fructicola 277 isolated from grapes in thecentral part of Israel (U.S. Pat. No. 6,994,849; NRRL Y-30752; e. g.formerly Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251isolated from infected nematode eggs in the Philippines (AGAL 89/030550;WO1991/02051; Crop Protection 27, 352-361, 2008; e. g. BioAct® fromBayer CropScience AG, Germany and MeloCon® from Certis, USA),Paenibacilus alvei NAS6G6 isolated from the rhizosphere of grasses inSouth Africa at least before 2008 (WO 2014/029697; NRRL B-50755; e.g.BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa),Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000sin Illinois, U.S.A. (ATCC SD-5833; Federal Register 76(22), 5808, Feb.2, 2011; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA),Penicilium bilaiae (also called P. bilaii) strains ATCC 18309 (=ATCC74319), ATCC 20851 and/or ATCC 22348 (=ATCC 74318) originally isolatedfrom soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J.Plant Sci. 78(1), 91-102, 1998; U.S. Pat. No. 5,026,417, WO 1995/017806;e. g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group,Canada), Reynoutria sachalinensis extract (EP 0307510 B1; e. g. Regalia®SC from Marrone BioInnovations, Davis, Calif., USA or Milsana® fromBioFa AG, Germany), Steinernema carpocapsae (e. g. Millenium® from BASFAgricultural Specialities Limited, UK), S. feltiae (e. g. Nemashield®from BioWorks, Inc., USA; Nemasys® from BASF Agricultural SpecialitiesLimited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014/124369;Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated inSouth Africa (NRRL 50759; also referred to as T. fertile; e. g.Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., SouthAfrica), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl57, 687-696, 2012; e. g. Plantshield® from BioWorks Inc., USA or SabrEx™from Advanced Biological Marketing Inc., Van Wert, OH, USA).

According to the invention, the solid material (dry matter) of thebiopesticides (with the exception of oils such as Neem oil) areconsidered as active components (e.g. to be obtained after drying orevaporation of the extraction or suspension medium in case of liquidformulations of the microbial pesticides).

In accordance with the present invention, the weight ratios andpercentages used herein for a biological extract such as Quillay extractare based on the total weight of the dry content (solid material) of therespective extract(s).

The total weight ratios of compositions comprising at least onemicrobial pesticide in the form of viable microbial cells includingdormant forms, can be determined using the amount of CFU of therespective microorganism to calculate the total weight of the respectiveactive component with the following equation that 1×10¹⁰ CFU equals onegram of total weight of the respective active component. Colony formingunit is measure of viable microbial cells, in particular fungal andbacterial cells. In addition, here “CFU” may also be understood as thenumber of (juvenile) individual nematodes in case of (entomopathogenic)nematode biopesticides, such as Steinernema feltiae.

When mixtures comprising microbial pesticides are employed in cropprotection, the application rates preferably range from about 1×106 to5×1015 (or more) CFU/ha, preferably from about 1×108 to about 1×1013CFU/ha, and even more preferably from about 1×109 to about 1×1012CFU/ha. In the case of (entomopathogenic) nematodes as microbialpesticides (e. g. Steinernema feltiae), the application rates preferablyrange inform about 1×105 to 1×1012 (or more), more preferably from 1×108to 1×1011, even more preferably from 5×108 to 1×1010 individuals (e. g.in the form of eggs, juvenile or any other live stages, preferably in aninfective juvenile stage) per ha.

When mixtures comprising microbial pesticides are employed in seedtreatment, the application rates with respect to plant propagationmaterial preferably range from about 1×106 to 1×1012 (or more) CFU/seed.Preferably, the concentration is about 1×106 to about 1×109 CFU/seed. Inthe case of the microbial pesticides II, the application rates withrespect to plant propagation material also preferably range from about1×107 to 1×1014 (or more) CFU per 100 kg of seed, preferably from 1×109to about 1×1012 CFU per 100 kg of seed.

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound of the present invention or amixture thereof.

An agrochemical composition comprises a pesticidally effective amount ofa compound of the present invention or a mixture thereof. The term“pesticidally effective amount” is defined below.

The compounds of the present invention or the mixtures thereof can beconverted into customary types of agro-chemical compositions, e. g.solutions, emulsions, suspensions, dusts, powders, pastes, granules,pressings, capsules, and mixtures thereof. Examples for compositiontypes are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g.EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes,pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS),pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG),insecticidal articles (e.g. LN), as well as gel formulations for thetreatment of plant propagation materials such as seeds (e.g. GF). Theseand further compositions types are defined in the “Catalogue ofpesticide formulation types and international coding system”, TechnicalMonograph No. 2, 6th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Examples for suitable auxiliaries are solvents, liquid carriers, solidcarriers or fillers, surfactants, dispersants, emulsifiers, wetters,adjuvants, solubilizers, penetration enhancers, protective colloids,adhesion agents, thickeners, humectants, repellents, attractants,feeding stimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclo-hexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharide powders, e.g. cellulose, starch;fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas; products of vegetable origin, e.g. cereal meal, treebark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemusifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkyl,naphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are homo- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compounds of the present invention on the target.Examples are surfactants, mineral or vegetable oils, and otherauxilaries. Further examples are listed by Knowles, Adjuvants andadditives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of a compound I according to the invention and 5-15 wt %wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/orin a water-soluble solvent (e.g. alcohols) up to 100 wt %. The activesubstance dissolves upon dilution with water.

ii) Dispersible Concentrates (DC)

5-25 wt % of a compound I according to the invention and 1-10 wt %dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt %organic solvent (e.g. cyclohexanone). Dilution with water gives adispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of a compound I according to the invention and 5-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in up to 100 wt % water-insoluble organicsolvent (e.g. aromatic hydrocarbon). Dilution with water gives anemulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I according to the invention and 1-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent(e.g. aromatic hydrocarbon). This mixture is introduced into up to 100wt % water by means of an emulsifying machine and made into ahomogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I according to theinvention are comminuted with addition of 2-10 wt % dispersants andwetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt % thickener (e.g. xanthan gum) and up to 100 wt % water to give afine active substance suspension. Dilution with water gives a stablesuspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a compound I according to the invention are ground finelywith addition of up to 100 wt % dispersants and wetting agents (e.g.sodium lignosulfonate and alcohol ethoxylate) and prepared aswater-dispersible or water-soluble granules by means of technicalappliances (e. g. extrusion, spray tower, fluidized bed). Dilution withwater gives a stable dispersion or solution of the active substance.

vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)

50-80 wt % of a compound I according to the invention are ground in arotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodiumlignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) andup to 100 wt % solid carrier, e.g. silica gel. Dilution with water givesa stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I according to theinvention are comminuted with addition of 3-10 wt % dispersants (e.g.sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)and up to 100 wt % water to give a fine suspension of the activesubstance. Dilution with water gives a stable suspension of the activesubstance.

ix) Microemulsion (ME)

5-20 wt % of a compound I according to the invention are added to 5-30wt % organic solvent blend (e.g. fatty acid dimethylamide andcyclohexanone), 10-25 wt % surfactant blend (e.g. alkohol ethoxylate andarylphenol ethoxylate), and water up to 100%. This mixture is stirredfor 1 h to produce spontaneously a thermodynamically stablemicroemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I according to theinvention, 0-40 wt % water insoluble organic solvent (e.g. aromatichydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate,methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radicalpolymerization initiated by a radical initiator results in the formationof poly(meth)acrylate microcapsules. Alternatively, an oil phasecomprising 5-50 wt % of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and anisocyanate monomer (e.g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). The addition of a polyamine (e.g.hexamethylenediamine) results in the formation of a polyureamicrocapsule. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.

xi) Dustable Powders (DP, DS)

1-10 wt % of a compound I according to the invention are ground finelyand mixed intimately with up to 100 wt % solid carrier, e.g. finelydivided kaolin.

xii) Granules (GR, FG)

0.5-30 wt % of a compound I according to the invention is ground finelyand associated with up to 100 wt % solid carrier (e.g. silicate).Granulation is achieved by extrusion, spray-drying or the fluidized bed.

xiii) Ultra-Low Volume Liquids (UL)

1-50 wt % of a compound I according to the invention are dissolved in upto 100 wt % organic solvent, e.g. aromatic hydrocarbon.

The compositions types i) to xi) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, and most preferably between 0.5 and 75%,by weight of active sub-stance. The active substances are employed in apurity of from 90% to 100%, preferably from 95% to 100% (according toNMR spectrum).

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and other pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, ifappropriate not until immediately prior to use (tank mix). These agentscan be admixed with the compositions according to the invention in aweight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually froma predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank andfurther auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e. g.components comprising compounds of the present invention and/or mixingpartners as defined above, may be mixed by the user in a spray tank andfurther auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e. g.components comprising compounds of the present invention and/or mixingpartners as defined above, can be applied jointly (e.g. after tank mix)or consecutively.

The compounds of the present invention are suitable for use inprotecting crops, plants, plant propagation materials, such as seeds, orsoil or water, in which the plants are growing, from attack orinfestation by animal pests. Therefore, the present invention alsorelates to a plant protection method, which comprises contacting crops,plants, plant propagation materials, such as seeds, or soil or water, inwhich the plants are growing, to be protected from attack or infestationby animal pests, with a pesticidally effective amount of a compound ofthe present invention.

The compounds of the present invention are also suitable for use incombating or controlling animal pests. Therefore, the present inventionalso relates to a method of combating or controlling animal pests, whichcomprises contacting the animal pests, their habitat, breeding ground,or food supply, or the crops, plants, plant propagation materials, suchas seeds, or soil, or the area, material or environment in which theanimal pests are growing or may grow, with a pesticidally effectiveamount of a compound of the present invention.

The compounds of the present invention are effective through bothcontact and ingestion. Furthermore, the compounds of the presentinvention can be applied to any and all developmental stages, such asegg, larva, pupa, and adult.

The compounds of the present invention can be applied as such or in formof compositions comprising them as defined above. Furthermore, thecompounds of the present invention can be applied together with a mixingpartner as defined above or in form of compositions comprising saidmixtures as defined above. The components of said mixture can be appliedsimultaneously, jointly or separately, or in succession, that isimmediately one after another and thereby creating the mixture “in situ”on the desired location, e.g. the plant, the sequence, in the case ofseparate application, generally not having any effect on the result ofthe control measures.

The application can be carried out both before and after the infestationof the crops, plants, plant propagation materials, such as seeds, soil,or the area, material or environment by the pests.

Suitable application methods include inter alia soil treatment, seedtreatment, in furrow application, and foliar application. Soil treatmentmethods include drenching the soil, drip irrigation (drip applicationonto the soil), dipping roots, tubers or bulbs, or soil injection. Seedtreatment techniques include seed dressing, seed coating, seed dusting,seed soaking, and seed pelleting. In furrow applications typicallyinclude the steps of making a furrow in cultivated land, seeding thefurrow with seeds, applying the pesticidally active compound to thefurrow, and closing the furrow. Foliar application refers to theapplication of the pesticidally active compound to plant foliage, e.g.through spray equipment. For foliar applications, it can be advantageousto modify the behavior of the pests by use of pheromones in combinationwith the compounds of the present invention. Suitable pheromones forspecific crops and pests are known to a skilled person and publiclyavailable from databases of pheromones and semiochemicals, such ashttp://www.pherobase.com.

As used herein, the term “contacting” includes both direct contact(applying the compounds/compositions directly on the animal pest orplant—typically to the foliage, stem or roots of the plant) and indirectcontact (applying the compounds/compositions to the locus, i.e. habitat,breeding ground, plant, seed, soil, area, material or environment inwhich a pest is growing or may grow, of the animal pest or plant).

The term “animal pest” includes arthropods, gastropods, and nematodes.Preferred animal pests according to the invention are arthropods,preferably insects and arachnids, in particular insects. Insects, whichare of particular relevance for crops, are typically referred to as cropinsect pests.

The term “crop” refers to both, growing and harvested crops.

The term “plant” includes cereals, e.g. durum and other wheat, rye,barley, triticale, oats, rice, or maize (fodder maize and sugarmaize/sweet and field corn); beet, e.g. sugar beet or fodder beet;fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears,plums, peaches, nectarines, almonds, cherries, papayas, strawberries,raspberries, blackberries or gooseberries; leguminous plants, such asbeans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed(oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoabeans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits,such as squashes, pumpkins, cucumber or melons; fiber plants, such ascotton, flax, hemp or jute; citrus fruit, such as oranges, lemons,grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce(e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots,onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers;lauraceous plants, such as avocados, cinnamon or camphor; energy and rawmaterial plants, such as corn, soybean, rapeseed, sugar cane or oilpalm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas;vines (table grapes and grape juice grape vines); hop; sweet leaf (alsocalled Stevia); natural rubber plants or ornamental and forestry plants,such as flowers (e.g. carnation, petunias, geranium/pelargoniums,pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) orevergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grassfor animal feed or ornamental uses. Preferred plants include potatoessugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton,soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits;vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans orsquashes.

The term “plant” is to be understood as including wild type plants andplants, which have been modified by either conventional breeding, ormutagenesis or genetic engineering, or by a combination thereof.

Plants, which have been modified by mutagenesis or genetic engineering,and are of particular commercial importance, include alfalfa, rapeseed(e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant,eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar,potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweetpepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize,soybean, cotton, wheat, and rice. In plants, which have been modified bymutagenesis or genetic engineering, one or more genes have beenmutagenized or integrated into the genetic material of the plant. Theone or more mutagenized or integrated genes are preferably selected frompat, epsps, cry1Ab, bar, cry1Fa2, cry1Ac, cry34Ab1, cry35AB1, cry3A,cryF, cry1F, mcry3a, cry2Ab2, cry3Bb1, cry1A.105, dfr, barnase,vip3Aa20, barstar, als, bxn, bp40, asn1, and ppo5. The mutagenesis orintegration of the one or more genes is performed in order to improvecertain properties of the plant. Such properties, also known as traits,include abiotic stress tolerance, altered growth/yield, diseaseresistance, herbicide tolerance, insect resistance, modified productquality, and pollination control. Of these properties, herbicidetolerance, e.g. imidazolinone tolerance, glyphosate tolerance, orglufosinate tolerance, is of particular importance. Several plants havebeen rendered tolerant to herbicides by mutagenesis, for exampleClearfield® oilseed rape being tolerant to imidazolinones, e.g.imazamox. Alternatively, genetic engineering methods have been used torender plants, such as soybean, cotton, corn, beets and oil seed rape,tolerant to herbicides, such as glyphosate and glufosinate, some ofwhich are commercially available under the trade names RoundupReady®(glyphosate) and LibertyLink® (glufosinate). Furthermore, insectresistance is of importance, in particular lepidopteran insectresistance and coleopteran insect resistance. Insect resistance istypically achieved by modifying plants by integrating cry and/or vipgenes, which were isolated from Bacillus thuringiensis (Bt), and codefor the respective Bt toxins. Genetically modified plants with insectresistance are commercially available under trade names includingWideStrike®, Bollgard®, Agrisure®, Herculex®, YieldGard®, Genuity®, andIntacta®. Plants may be modified by mutagenesis or genetic engineeringeither in terms of one property (singular traits) or in terms of acombination of properties (stacked traits). Stacked traits, e.g. thecombination of herbicide tolerance and insect resistance, are ofincreasing importance. In general, all relevant modified plants inconnection with singular or stacked traits as well as detailedinformation as to the mutagenized or integrated genes and the respectiveevents are available from websites of the organizations “InternationalService for the Acquisition of Agri-biotech Applications (ISAAA)”(http://www.isaaa.org/gmapprovaldatabase) and “Center for EnvironmentalRisk Assessment (CERA)” (http://cera-gmc.org/GMCropDatabase).

It has surprisingly been found that the pesticidal activity of thecompounds of the present invention may be enhanced by the insecticidaltrait of a modified plant. Furthermore, it has been found that thecompounds of the present invention are suitable for preventing insectsto become resistant to the insecticidal trait or for combating pests,which already have become resistant to the insecticidal trait of amodified plant. Moreover, the compounds of the present invention aresuitable for combating pests, against which the insecticidal trait isnot effective, so that a complementary insecticidal activity canadvantageously be used.

The term “plant propagation material” refers to all the generative partsof the plant such as seeds and vegetative plant material such ascuttings and tubers (e.g. potatoes), which can be used for themultiplication of the plant. This includes seeds, roots, fruits, tubers,bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlingsand young plants, which are to be transplanted after germination orafter emergence from soil, may also be included. These plant propagationmaterials may be treated prophylactically with a plant protectioncompound either at or before planting or transplanting.

The term “seed” embraces seeds and plant propagules of all kindsincluding but not limited to true seeds, seed pieces, suckers, corms,bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, andmeans in a preferred embodiment true seeds.

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment, in furrow application or of applicationto the pests dwelling place or nest, the quantity of active ingredientranges from 0.0001 to 500 g per 100 m², preferably from 0.001 to 20 gper 100 m².

For use in treating crop plants, e.g. by foliar application, the rate ofapplication of the active ingredients of this invention may be in therange of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg perhectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 gper hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40to 50 g per hectare.

The compounds of the present invention are particularly suitable for usein the treatment of seeds in order to protect the seeds from insectpests, in particular from soil-living insect pests, and the resultingseedling's roots and shoots against soil pests and foliar insects. Thepresent invention therefore also relates to a method for the protectionof seeds from insects, in particular from soil insects, and of theseedling's roots and shoots from insects, in particular from soil andfoliar insects, said method comprising treating the seeds before sowingand/or after pregermination with a compound of the present invention.The protection of the seedling's roots and shoots is preferred. Morepreferred is the protection of seedling's shoots from piercing andsucking insects, chewing insects and nematodes.

The term “seed treatment” comprises all suitable seed treatmenttechniques known in the art, such as seed dressing, seed coating, seeddusting, seed soaking, seed pelleting, and in-furrow applicationmethods. Preferably, the seed treatment application of the activecompound is carried out by spraying or by dusting the seeds beforesowing of the plants and before emergence of the plants.

The present invention also comprises seeds coated with or containing theactive compound. The term “coated with and/or containing” generallysignifies that the active ingredient is for the most part on the surfaceof the propagation product at the time of application, although agreater or lesser part of the ingredient may penetrate into thepropagation product, depending on the method of application. When thesaid propagation product is (re)planted, it may absorb the activeingredient.

Suitable seed is for example seed of cereals, root crops, oil crops,vegetables, spices, ornamentals, for example seed of durum and otherwheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet andfield corn), soybeans, oil crops, crucifers, cotton, sunflowers,bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet,eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks,pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons,Brassica species, melons, beans, peas, garlic, onions, carrots, tuberousplants such as potatoes, sugar cane, tobacco, grapes, petunias,geranium/pelargoniums, pansies and impatiens.

In addition, the active compound may also be used for the treatment ofseeds from plants, which have been modified by mutagenisis or geneticengineering, and which e.g. tolerate the action of herbicides orfungicides or insecticides. Such modified plants have been described indetail above.

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, suspoemulsions (SE), powders for drytreatment DS, water dispersible powders for slurry treatment WS,water-soluble powders SS and emulsion ES and EC and gel formulation GF.These formulations can be applied to the seed diluted or undiluted.Application to the seeds is carried out before sowing, either directlyon the seeds or after having pregerminated the latter. Preferably, theformulations are applied such that germination is not included.

The active substance concentrations in ready-to-use formulations, whichmay be obtained after two-to-tenfold dilution, are preferably from 0.01to 60% by weight, more preferably from 0.1 to 40% by weight.

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of the compounds of the presentinvention for seed treatment usually comprise from 0.1 to 80% by weight(1 to 800 g/1) of the active ingredient, from 0.1 to 20% by weight (1 to200 g/1) of at least one surfactant, e.g. 0.05 to 5% by weight of awetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% byweight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% byweight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40%by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent),optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of athickener, optionally from 0.1 to 2% of an anti-foam agent, andoptionally a preservative such as a biocide, antioxidant or the like,e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to100% by weight.

In the treatment of seed, the application rates of the compounds of theinvention are generally from 0.1 g to 10 kg per 100 kg of seed,preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 gto 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg ofseed.

The invention therefore also relates to seed comprising a compound ofthe present invention, or an agriculturally useful salt thereof, asdefined herein. The amount of the compound of the present invention orthe agriculturally useful salt thereof will in general vary from 0.1 gto 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg ofseed, in particular from 1 g to 1000 g per 100 kg of seed. For specificcrops such as lettuce the rate can be higher.

The compounds of the present invention may also be used for improvingthe health of a plant. Therefore, the present invention also relates toa method for improving plant health by treating a plant, plantpropagation material and/or the locus where the plant is growing or isto grow with an effective and non-phytotoxic amount of a compound of thepresent invention.

As used herein “an effective and non-phytotoxic amount” means that thecompound is used in a quantity which allows to obtain the desired effectbut which does not give rise to any phytotoxic symptom on the treatedplant or on the plant grown from the treated propagule or treated soil.

The terms “plant” and “plant propagation material” are defined above.

“Plant health” is defined as a condition of the plant and/or itsproducts which is determined by several aspects alone or in combinationwith each other such as yield (for example increased biomass and/orincreased content of valuable ingredients), quality (for exampleimproved content or composition of certain ingredients or shelf life),plant vigour (for example improved plant growth and/or greener leaves(“greening effect”), tolerance to abiotic (for example drought) and/orbiotic stress (for example disease) and production efficiency (forexample, harvesting efficiency, processability).

The above identified indicators for the health condition of a plant maybe interdependent and may result from each other. Each indicator isdefined in the art and can be determined by methods known to a skilledperson.

The compounds of the invention are also suitable for use againstnon-crop insect pests. For use against said non-crop pests, compounds ofthe present invention can be used as bait composition, gel, generalinsect spray, aerosol, as ultra-low volume application and bed net(impregnated or surface applied). Furthermore, drenching and roddingmethods can be used.

As used herein, the term “non-crop insect pest” refers to pests, whichare particularly relevant for non-crop targets, such as ants, termites,wasps, flies, ticks, mosquitos, crickets, or cockroaches.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). The bait employed in the composition is a product, which issufficiently attractive to incite insects such as ants, termites, wasps,flies, mosquitos, crickets etc. or cockroaches to eat it. Theattractiveness can be manipulated by using feeding stimulants or sexpheromones. Food stimulants are chosen, for example, but notexclusively, from animal and/or plant proteins (meat-, fish- or bloodmeal, insect parts, egg yolk), from fats and oils of animal and/or plantorigin, or mono-, oligo- or polyor-ganosaccharides, especially fromsucrose, lactose, fructose, dextrose, glucose, starch, pectin or evenmolasses or honey. Fresh or decaying parts of fruits, crops, plants,animals, insects or specific parts thereof can also serve as a feedingstimulant. Sex pheromones are known to be more insect specific. Specificpheromones are described in the literature (e.g.http://www.pherobase.com), and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredientis from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to5% weight % of active compound.

Formulations of the compounds of the present invention as aerosols (e.gin spray cans), oil sprays or pump sprays are highly suitable for thenon-professional user for controlling pests such as flies, fleas, ticks,mosquitos or cockroaches. Aerosol recipes are preferably composed of theactive compound, solvents, furthermore auxiliaries such as emulsifiers,perfume oils, if appropriate stabilizers, and, if required, propellants.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of the present invention and its respective compositionscan also be used in mosquito and fumigating coils, smoke cartridges,vaporizer plates or long-term vaporizers and also in moth papers, mothpads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of the present invention and itsrespective compositions also comprise treating surfaces of huts andhouses, air spraying and impregnation of curtains, tents, clothingitems, bed nets, tsetse-fly trap or the like. Insecticidal compositionsfor application to fibers, fabric, knitgoods, nonwovens, nettingmaterial or foils and tarpaulins preferably comprise a mixture includingthe insecticide, optionally a repellent and at least one binder.

The compounds of the present invention and its compositions can be usedfor protecting wooden materials such as trees, board fences, sleepers,frames, artistic artifacts, etc. and buildings, but also constructionmaterials, furniture, leathers, fibers, vinyl articles, electric wiresand cables etc. from ants and/or termites, and for controlling ants andtermites from doing harm to crops or human being (e.g. when the pestsinvade into houses and public facilities).

Customary application rates in the protection of materials are, forexample, from 0.001 g to 2000 g or from 0.01 g to 1000 g of activecompound per m² treated material, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

The compounds of the the present invention are especially suitable forefficiently combating animal pests such as arthropods, gastropods andnematodes including but not limited to: insects from the order ofLepidoptera, for example Achroia grisella, Acleris spp. such as A.fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronictamajor, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas,Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A.orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicusdispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyeloistransitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsialineatella, Anisota senatoria, Antheraea pernyi, Anticarsia (=Thermesia)spp. such as A. gemmatalis; Apamea spp., Aproaerema modicella, Archipsspp. such as A. argyrospila, A. fuscocupreanus, A. rosana, A.xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp.such as A. velutinana; Athetis mindara, Austroasca viridigrisea,Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedelliaspp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberella,Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C.podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis,Caloptilis theivora, Capua reticulana, Carposina spp. such as C.niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobiabrumata, Chilo spp. such as C. indicus, C. suppressalis, C. partellus;Choreutis pariana, Choristoneura spp. such as C. conflictana, C.fumiferana, C. longicellana, C. murinana, C. occidentalis, C. rosaceana;Chrysodeixis (=Pseudoplusia) spp. such as C. eriosoma, C. includens;Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocismedinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Coliaseurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp.,Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus,Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis,Cydia (=Carpocapsa) spp. such as C. pomonella, C. latiferreana; Dalacanoctuides, Datana integerrima, Dasychira pinicola, Dendrolimus spp. suchas D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphaniaspp. such as D. nitidalis, D. hyalinata; Diatraea grandiosella, Diatraeasaccharalis, Diphthera festiva, Earias spp. such as E. insulana, E.vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curalis,Elasmopalpus lignosellus, Eldana saccharna, Endopiza viteana, Ennomossubsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E.elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannistiliaria, Erionota thrax, Etiella spp., Eulia spp., Eupoeciliaambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana,Faronta albilinea, Feltia spp. such as F. subterranean; Galleriamellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G.molesta, G. inopinata; Halysidota spp., Harrisina americana, Hedyleptaspp., Helicoverpa spp. such as H. armigera (=Heliothis armigera), H. zea(=Heliothis zea); Heliothis spp. such as H. assulta, H. subflexa, H.virescens; Hellula spp. such as H. undalis, H. rogatalis; Helocoverpagelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hiberniadefoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homonamagnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella,Hyponomeuta malinellus, Kakivoria flavofasciata, Keiferialycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscellarialugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivoraglycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma salicis,Leucoptera spp. such as L. coffeella, L. scitella; Leuminivoralycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattiaocto (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotisalbicosta, Loxostege spp. such as L. sticticalis, L. cereralis;Lymantria spp. such as L. dispar, L. monacha; Lyonetia clerkella,Lyonetia prunifoliella, Malacosoma spp. such as M. americanum, M.callifornicum, M. constrictum, M neustria; Mamestra spp. such as M.brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M.quinquemaculata, M. sexta Marasmia spp, Marmara spp., Maruca testulalis,Megalopyge lanata, Melanchra picta, Melanitis leda, Mocis spp. such asM. lapites, M. repanda; Mocis latipes, Monochroa fragariae, Mythimnaseparata, Nemapogon cloacella, Neoleucnodes elegantalis, Nepytia spp.,Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis,Operophtera brumata, Orgyia pseudotsugata, Oria spp., Orthagathyrisalis, Ostrinia spp. such as O. nubilalis; Oulema oryzae,Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris,Papiio cresphontes, Paramyelois transitella, Paranthrene regalis,Paysandisia archon, Pectinophora spp. such as P. gossypiella; Peridromasaucia, Perileucoptera spp., such as P. coffeella; Phalera bucephala,Phryganidia californica, Phthorimaea spp. such as P. operculella;Phyllocnistis citrella, Phyllonorycter spp. such as P. blancardella, P.crataegella, P. ssiki, P. ringoniella; Pieris spp. such as P. brassicae,P. rapae, P. napi; Pilocrocis trpunctata, Plathypena scabra, Platynotaspp. such as P. flavedana, P. idaeusalis, P. stultana; Platyptiliacarduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp,Plutella maculipennis, Plutella xylostella, Pontia protodica, Praysspp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. such as P.sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Richiaalbicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodesaegrotata, Schizura concinna, Schoenobius spp., Schreckensteiniafestaliella, Scirpophaga spp. such as S. incertulas, S. innotata; Scotiasegetum, Sesamia spp. such as S. inferens, Seudyra subflava, Sitotrogacerealella, Sparganothis pilleriana, Spilonota lechraspis, S. ocellana,Spodoptera (=Lamphygma) spp. such as S. cosmoides, S. erdania, S. exgua,S. frugiperda, S. latisfascia, S. littoralis, S. litura, S. omithogalli;Stigmella spp., Stomopteryx subsecivella, Strymon bazochi, Syleptaderogata, Synanthedon spp. such as S. exitiosa, Tecia solanivora,Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia)leucotreta, Thaumetopoea pityocampa, Thecla spp., Theresimimaampelophaga, Thyrintena spp, Tildenia inconspicuella, Tinea spp. such asT. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. such asT. viridana; Trichophaga tapetzella, Trichoplusia spp. such as T. ni;Tuta (=Scrobipalpula) absoluta, Udea spp. such as U. rubigalis, U.rubigalis; Virachola spp., Yponomeuta padella, and Zeirapheracanadensis;

insects from the order of Coleoptera, for example Acalymma vittatum,Acanthoscehdes obtectus, Adoretus spp., Agelastica ani, Agrilus spp.such as A. anxius, A. planipennis, A. sinuatus; Agriotes spp. such as A.fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus,Amphimallus solstitialis, Anisandrus dispar, Anisoplia austraca, Anobiumpunctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophora spp. suchas A. glabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A.pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp.,Athous haemorrhoidalis, Atomaria spp. such as A. linearns; Attagenusspp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata,Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B.rufimanus; Byctiscus betulae, Callidiellum rufpenne, Callopistriafloridensis, Callosobruchus chinensis, Cameraria ohridella, Cassidanebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. suchas C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus,Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar,Cosmopolites spp., Costelytra zealandica, Crioceris asparagi,Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such asC. destructor, Curculio spp., Cylindrocopturus spp., Cyclocephala spp.,Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. suchas D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D.vrgfera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera,Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis),Enaphalodes rufulus, Epilachna spp. such as E. varvestis, E.vigintioctomaculata; Epitri spp. such as E. hirtipennis, E. similars;Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbiumpsylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator,Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp.such as H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemusspp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne,Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L.melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea,Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodesspp., Lyctus spp. such as L. bruneus; Liogenys fuscus, Macrodactylusspp. such as M. subspinosus; Maladera matrida, Megaplatypus mutates,Megascelis spp., Melanotus communis, Meligethes spp. such as M. aeneus;Melolontha spp. such as M. hippocastani, M. melolontha; Metamasiushemipterus, Microtheca spp., Migdolus spp. such as M. fryanus,Monochamus spp. such as M. alternatus; Naupactus xanthographus, Niptushololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros,Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sulcatus,Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P.cochlearnae; Phoracantha recurva, Phyllobius pyri, Phylloperthahorticola, Phyllophaga spp. such as P. helleri Phyllotreta spp. such asP. chrysocephala, P. nemorum, P. striolata, P. vittula; Phylloperthahorticola, Popila japonica, Premnotrypes spp., Psacothea hilars,Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp.,Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp.such as R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R.vulneratus; Saperda candida, Scolytus schevyrewi, Scyphophorusacupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S.oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobiumpaniceum, Sternechus spp. such as S. subsignatus; Strophomorphusctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor,Tenebrioides mauretanicus, Tribolium spp. such as T. castaneum;Trogoderma spp., Tychius spp., Xylotrechus spp. such as X. pyrrhoderus;and, Zabrus spp. such as Z. tenebrioides;

insects from the order of Diptera for example Aedes spp. such as A.aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp.such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A.leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A.sinensis; Bactrocera invadens, Bibio hortulanus, Calliphoraerythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp.such as C. bezziana, C. hominivorax, C. macellara; Chrysops atlanticus,Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as C.hominivorax; Contarnia spp. such as C. sorghicola; Cordylobiaanthropophaga, Culex spp. such as C. nigripalpus, C. pipiens, C.quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicoides furens,Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae,Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. suchas D. antique, D. coarctata, D. platura, D. radicum; Dermatobia hominis,Drosophila spp. such as D. suzukii, Fannia spp. such as F. caniculars;Gastraphilus spp. such as G. intestinalis; Geomyza tipunctata, Glossinaspp. such as G. fuscipes, G. morsitans, G. palpalis, G. tachinoides;Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyiaspp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppoboscaspp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such asL. sativae, L. trifolii; Lucilia spp. such as L. caprina, L. cuprina, L.sericata: Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. suchas M. destructor; Musca spp. such as M. autumnalis, M. domestica;Muscina stabulans, Oestrus spp. such as O. ovis; Opomyza florum,Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami,Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae,P. coarctata; Phytomyza gymnostoma, Prosimulium mixtum, Psila rosae,Psorophora columbiae, Psorophora discolor, Rhagoletis spp. such as R.cerasi, R. cingulate, R. indifferens, R. mendax, R. pomonella; Rivelliaquadrifasciata, Sarcophaga spp. such as S. haemorrhoidalis; Simuliumvittatum, Sitodiplosis mosellana, Stomoxys spp. such as S. calcitrans;Tabanus spp. such as T. atratus, T. bovinus, T. lineola, T. similis;Tannia spp., Thecodiplosis japonensis, Tipula oleracea, Tipula paludosa,and Wohlfahrtia spp;

insects from the order of Thysanoptera for example, Baliothripsbiformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothripsamericanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F.occidentalis, F. tritici; Heliothrips spp., Hercinothrips femoralis,Kakothrips spp., Microcephalothrips abdominalis, Neohydatothripssamayunkur, Pezothrips kellyanus, Rhipiphorothrps cruentatus,Scirtothrps spp. such as S. citri, S. dorsalis, S. perseae;Stenchaetothrips spp, Taeniothrips cardamoni, Taeniothrps inconsequens,Thrips spp. such as T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T.parvispinus, T. tabaci;

insects from the order of Hemiptera for example, Acizzia jamatonica,Acrosternum spp. such as A. hilare; Acyrthosipon spp. such as A.onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocorisspp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp.,Aulacorthum solani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicusdisperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp.,Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp.,Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as A. craccivora,A. fabae, A. forbesi, A. gossypii, A. grossulariae, A. maidiradicis, A.pomi, A. sambuci, A. schneiden, A. spiraecola; Arboridia apicalis,Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp.,Aulacaspis yasumatsui, Aulacorthum solani, Bactericera cockerelli(Paratrioza cockerei), Bemisia spp. such as B. argentifolii, B. tabaci(Aleurodes tabaci); Blissus spp. such as B. leucopterus; Brachycaudusspp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola;Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae,Cacopsylla spp. such as C. fulguralis, C. pyricola (Psylla piri);Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorushorni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp.,Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypii,Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii,Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimexspp. such as C. hemipterus, C. lectularius; Coccomytilus halli, Coccusspp. such as C. hesperidum, C. pseudomagnoliarum; Corythucha arcuata,Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum,Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbulusspp., Dasynus pipers, Dialeurodes spp. such as D. citrifolii; Dalbulusmaidis, Diaphorina spp. such as D. citri; Diaspis spp. such as D.bromeliae; Dichelops furcatus, Diconocoris hewetti, Doralis spp.,Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp.such as D. plantaginea, D. pyri, D. radicola; Dysaulacorthumpseudosolani, Dysdercus spp. such as D. cingulatus, D. intermedius;Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. such as E.fabae, E. solana; Epidiaspis leperii, Eriosoma spp. such as E.lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E.integriceps; Euscelis bilobatus, Euschistus spp. such as E. heros, E.impictiventris, E. servus; Fiornia theae, Geococcus coffeae, Glycaspisbrimblecombei, Halyomorpha spp. such as H. halys; Heliopeltis spp.,Homalodisca vitripennis (H. coagulata), Horcias noblellus, Hyalopteruspruni, Hyperomyzus lactucae, Icerya spp. such as I. purchase; Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Leptocorisaspp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L.hesperus, L. lineolaris, L. pratensis; Maconellicoccus hirsutus,Marchalina hellenica, Macropes excavatus, Macrosphum spp. such as M.rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarvafimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius,Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae,Metcafiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. suchas M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians;Nasonovia ribis-nigri, Neotoxoptera formosana, Neomegalotomus spp,Nephotettix spp. such as N. malayanus, N. nigropictus, N. parvus, N.virescens; Nezara spp. such as N. viridula; Nilaparvata lugens, Nysiushutton, Oebalus spp. such as O. pugnax; Oncometopia spp., Ortheziapraelonga, Oxycaraenus hyalinipennis, Parabemisia myricae, Parlatoriaspp., Parthenolecanium spp. such as P. corni, P. persicae; Pemphigusspp. such as P. bursarius, P. populivenae; Peregrinus maidis,Perkinsiella saccharicida, Phenacoccus spp. such as P. aceris, P.gossypii; Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. suchas P. devastatrix, Piesma quadrata, Piezodorus spp. such as P.guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P. citri, P.ficus; Prosapia bicincta, Protopulvinaria pyriformis, Psallus seriatus,Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such asP. comstocki; Psylla spp. such as P. mali; Pteromalus spp., Pulvinariaamygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus;Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecusamericanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp.such as R. pseudobrassicas, R. insertum, R. maids, R. padi; Sagatodesspp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphismali, Scaptocoris spp., Scaphoides titanus, Schizaphis graminum,Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus,Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis,Spissistilus festinus (=Stictocephala festina), Stephanitis nashi,Stephanitis pyrioides, Stephanitis takeyai, Tenalaphara malayensis,Tetraleurodes perseae, Therioaphis maculate, Thyanta spp. such as T.accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. suchas T. aurantii; Trialeurodes spp. such as T. abutilonea, T. ricini, T.vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp.such as U. citri, U. yanonensis; and Viteus vitifolii, Insects from theorder Hymenoptera for example Acanthomyops interjectus, Athalia rosae,Atta spp. such as A. capiguara, A. cephalotes, A. cephalotes, A.laevigata, A. robusta, A. sexdens, A. texana, Bombus spp., Brachymyrmexspp., Camponotus spp. such as C. floridanus, C. pennsylvanicus, C.modoc; Cardiocondyla nuda, Chalibion sp, Crematogaster spp., Dasymutillaoccidentalis, Diprion spp., Dolichovespula maculata, Dorymyrmex spp.,Dryocosmus kuriphilus, Formica spp., Hoplocampa spp. such as H. minuta,H. testudinea; Iridomyrmex humilis, Lasius spp. such as L. niger,Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp.such as M. pharaonis, Monomorium, Nylandra fulva, Pachycondylachinensis, Paratrechina longicornis, Paravespula spp., such as P.germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P.megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus,Polistes rubiginosa, Prenolepis impairs, Pseudomyrmex gracilis,Schelipron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, S.invicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphexspp., Tapinoma spp. such as T. melanocephalum, T. sessile; Tetramoriumspp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro;Vespula spp. such as V. squamosal; Wasmannia auropunctata, Xylocopa sp;

Insects from the order Orthoptera for example Acheta domesticus,Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp.,Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. suchas G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis,Kraussaria angulifera, Locusta spp. such as L. migratoria, L. pardalina;Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M.sanguinipes, M. spretus; Nomadacris septemfasciata, Oedaleussenegalensis, Scapteriscus spp., Schistocerca spp. such as S. Americana,S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerusvariegatus;

Pests from the Class Arachnida for example Acari, e.g. of the familiesArgasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A.americanum, A. variegatum, A. maculatum), Argas spp. such as A.persicu), Boophilus spp. such as B. annulatus, B. decoloratus, B.microplus, Dermacentor spp. such as D. siivarum, D. andersoni, D.variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as I.ricinus, I. rubicundus, I. scapularis, I. holocyclus, L. pacificus,Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O.hermsi, O. turcata, Ornithonyssus bacoti, Otobus megnni, Dermanyssusgallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R.sanguineus, R. appendiculatus, Rhipicephalus evertsi, Rhizoglyphus spp.,Sarcoptes spp. such as S. Scabiei; and Family Eriophyidae includingAceria spp. such as A. sheldoni, A. anthocoptes, Acallitus spp., Aculopsspp. such as A. lycopersici, A. pelekassi; Aculus spp. such as A.schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptrutaoleivora; Eriophytes ribis and Eriophyes spp. such as Eriophyessheldoni; Family Tarsonemidae including Hemitarsonemus spp., Phytonemuspallidus and Polyphagotarsonemus latus, Stenotarsonemus spp.Steneotarsonemus spinki; Family Tenuipalpidae including Brevipalpus spp.such as B. phoenicis; Family Tetranychidae including Eotetranychus spp.,Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp.such as T. cinnabarinus, T. evansi, T. kanzawai, T. pacificus, T.phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychusspp. such as P. ulmi, P. citri; Metatetranychus spp. and Oligonychusspp. such as O. pratensis, O. perseae, Vasates lycopersici; Raoiellaindica, Family Carpoglyphidae including Carpoglyphus spp.; Penthaleidaespp. such as Halotydeus destructor; Family Demodicidae with species suchas Demodex spp.; Family Trombicidea including Trombicula spp.; FamilyMacronyssidae including Ornothonyssus spp.; Family Pyemotidae includingPyemotes tritici; Tyrophagus putrescentiae; Family Acaridae includingAcarus siro; Family Araneida including Latrodectus mactans, Tegenaraagrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum andLoxosceles reclusa;

Pests from the Phylum Nematoda, for example, plant parasitic nematodessuch as root-knot nematodes, Meloidogyne spp. such as M. hapla, M.incognita, M. javanica; cyst-forming nematodes, Globodera spp. such asG. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H.schachtii, H. trifoii; Seed gall nematodes, Anguina spp.; Stem andfoliar nematodes, Aphelenchoides spp. such as A. besseyi; Stingnematodes, Belonolaimus spp. such as B. longicaudatus; Pine nematodes,Bursaphelenchus spp. such as B. lignicolus, B. xylophilus; Ringnematodes, Criconema spp., Criconemella spp. such as C. xenoplax and C.ornata; and, Criconemoides spp. such as Criconemoides informis;Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp. such as D.destructor, D. dipsaci; Awl nematodes, Dolichodorus spp.; Spiralnematodes, Heliocotylenchus multicinctus; Sheath and sheathoidnematodes, Hemicycliophora spp. and Hemicriconemoides spp.;Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknotnematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. such as L.elongatus; Lesion nematodes, Pratylenchus spp. such as P. brachyurus, P.neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes,Radopholus spp. such as R. similis; Rhadopholus spp.; Rhodopholus spp.;Reniform nematodes, Rotylenchus spp. such as R. robustus, R. reniformis;Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T.obtusus, T. primitivus; Paratrichodorus spp. such as P. minor; Stuntnematodes, Tylenchorhynchus spp. such as T. claytoni, T. dubius; Citrusnematodes, Tylenchulus spp. such as T. semipenetrans; Dagger nematodes,Xiphinema spp.; and other plant parasitic nematode species;

Insects from the order Isoptera for example Calotermes flavicois,Coptotermes spp. such as C. formosanus, C. gestroi, C. acinaciformis;Cornitermes cumulans, Cryptotermes spp. such as C. brevis, C. cavifrons;Globitermes sulfureus, Heterotermes spp. such as H. aureus, H.longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp.,Incisitermes spp. such as I. minor, I. Snyder, Marginitermes hubbardi,Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N.opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsisspp. such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. suchas R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R.lucfugus, R. santonensis, R. virginicus; Termes natalensis,

Insects from the order Blattaria for example Blatta spp. such as B.orientalis, B. lateralis; Blattella spp. such as B. asahinae, B.germanica; Leucophaea maderae, Panchlora nivea, Periplaneta spp. such asP. americana, P. australasiae, P. brunnea, P. fuligginosa, P. japonica;Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana,Pycnoscelus surinamensis,

Insects from the order Siphonoptera for example Cediopsylla simples,Ceratophyllus spp., Ctenocephalides spp. such as C. felis, C. canis,Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans,and Nosopsyllus fasciatus,

Insects from the order Thysanura for example Lepisma saccharina,Ctenolepisma urbana, and Thermobia domestica,

Pests from the class Chilopoda for example Geophilus spp., Scutigeraspp. such as Scutigera coleoptrata;

Pests from the class Diplopoda for example Blaniulus guttulatus, Julusspp., Narceus spp.,

Pests from the class Symphyla for example Scutigerella immaculata,

Insects from the order Dermaptera, for example Forficula auricularia,

Insects from the order Collembola, for example Onychiurus spp., such asOnychiurus armatus,

Pests from the order Isopoda for example, Armadillidium vulgare, Oniscusasellus, Porcellio scaber,

Insects from the order Phthiraptera, for example Damalinia spp.,Pediculus spp. such as Pediculus humanus capitis, Pediculus humanuscorpors, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp.such as Haematopinus eurysternus, Haematopinus suis; Linognathus spp.such as Linognathus vituli; Bovicola bovis, Menopon gallinae,Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds offormula (I) include: from the Phylum Mollusca, class Bivalvia, forexample, Dreissena spp.; class Gastropoda, for example, Arion spp.,Biomphalaria spp., Bullinus spp., Deroceras spp., Galba spp., Lymnaeaspp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from theclass of the helminths, for example, Ancylostoma duodenale, Ancylostomaceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascarislumbricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomumspp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp.,Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis,Echinococcus granulosus, Echinococcus multilocularis, Enterobiusvermicularis, Faciola spp., Haemonchus spp. such as Haemonchuscontortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., LoaLoa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp.,Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomenspp., Strongyloides fuelleborni, Strongyloides stercora lis,Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis,Trichinella nativa, Trichinella britovi, Trichinella nelsoni,Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichiura,Wuchereria bancrofti.

The compounds of the present invention are suitable for use in treatingor protecting animals against infestation or infection by parasites.Therefore, the present invention also relates to the use of a compoundof the present invention for the manufacture of a medicament for thetreatment or protection of animals against infestation or infection byparasites. Furthermore, the present invention relates to a method oftreating or protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasiticidally effectiveamount of a compound of the present invention.

The present invention also relates to the non-therapeutic use ofcompounds of the present invention for treating or protecting animalsagainst infestation and infection by parasites. Moreover, the presentinvention relates to a non-therapeutic method of treating or protectinganimals against infestation and infection by parasites, which comprisesapplying to a locus a parasiticidally effective amount of a compound ofthe present invention.

The compounds of the present invention are further suitable for use incombating or controlling parasites in and on animals. Furthermore, thepresent invention relates to a method of combating or controllingparasites in and on animals, which comprises contacting the parasiteswith a parasitically effective amount of a compound of the presentinvention.

The present invention also relates to the non-therapeutic use ofcompounds of the present invention for controlling or combatingparasites. Moreover, the present invention relates to a nontherapeuticmethod of combating or controlling parasites, which comprises applyingto a locus a parasiticidally effective amount of a compound of thepresent invention.

The compounds of the present invention can be effective through bothcontact (via soil, glass, wall, bed net, carpet, blankets or animalparts) and ingestion (e.g. baits). Furthermore, the compounds of thepresent invention can be applied to any and all developmental stages.

The compounds of the present invention can be applied as such or in formof compositions comprising the compounds of the present invention.

The compounds of the present invention can also be applied together witha mixing partner, which acts against pathogenic parasites, e.g. withsynthetic coccidiosis compounds, polyetherantibiotics such as Amprolium,Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid,Narasin or Semduramicin, or with other mixing partners as defined above,or in form of compositions comprising said mixtures.

The compounds of the present invention and compositions comprising themcan be applied orally, parenterally or topically, e.g. dermally. Thecompounds of the present invention can be systemically ornon-systemically effective.

The application can be carried out prophylactically, therapeutically ornon-therapeutically. Furthermore, the application can be carried outpreventively to places at which occurrence of the parasites is expected.

As used herein, the term “contacting” includes both direct contact(applying the compounds/compositions directly on the parasite, includingthe application directly on the animal or excluding the applicationdirectly on the animal, e.g. at it's locus for the latter) and indirectcontact (applying the compounds/compositions to the locus of theparasite). The contact of the parasite through application to its locusis an example of a non-therapeutic use of the compounds of the presentinvention.

The term “locus” means the habitat, food supply, breeding ground, area,material or environment in which a parasite is growing or may growoutside of the animal.

As used herein, the term “parasites” includes endo- and ectoparasites.In some embodiments of the present invention, endoparasites can bepreferred. In other embodiments, ectoparasites can be preferred.Infestations in warm-blooded animals and fish include, but are notlimited to, lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of the present invention are especially useful forcombating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus; cockroaches (Blattaria—Blattodea), e.g. Blattella germanica,Blattella asahinae, Perplaneta americana, Periplaneta japonica,Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae,and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegypti,Aedes albopictus, Aedes vexans, Anastrepha ludens, Anophelesmaculipennis, Anopheles crucians, Anopheles albimanus, Anophelesgambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus,Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana,Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysopssilacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobiaanthropophaga, Culicoides furens, Culex pipiens, Culex nignpalpus, Culexquinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura,Dermatobia hominis, Fannia caniculars, Gasterophilus intestinalis,Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossinatachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelatesspp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Luciliacuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Muscadomestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes,Psorophora columbiae, Psorophora discolor, Prosimulium mixtum,Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxyscalcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, andTabanus similis; lice (Phthiraptera), e.g. Pediculus humanus capitis,Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus,Haematopinus suis, Linognathus vituli Bovicola bovis, Menopon gallinae,Menacanthus stramineus and Solenopotes capillatus; ticks and parasiticmites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodesholocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentorandersoni, Dermacentor variabilis, Amblyomma americanum, Ambryommamaculatum, Ornithodorus hermsi, Ornithodorus turicata and parasiticmites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssusgallinae; Actinedida (Prostigmata) und Acaridida (Astigmata), e.g.Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp.,Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp.,Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp.,Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., andLaminosioptes spp; Bugs (Heteropterida): Cimex lectularius, Cimexhemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp.,Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g. Haematopinusspp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotesspp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g.Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicolaspp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida),e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp.,Capillaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyloides spp.,Helicephalobus spp.; Strongylida, e.g. Strongylus spp., Ancylostomaspp., Necatoramericanus, Bunostomum spp. (Hookworm), Trichostrongylusspp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirusspp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp.,Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurusdentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp.,Globocephalus spp., Necator spp., Metastrongylus spp., Muelleriuscapillaris, Protostrongylus spp., Angiostrongylus spp.,Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophymarenale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides,Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobiusvermicularis (Threadworm), Toxocara canis, Toxascaris leonine,Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculusmedinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereriaspp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonemaspp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronemaspp.; Thorny headed worms (Acanthocephaa), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians(Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloidesmagna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski,Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alariaalata, Paragonimus spp., and Nanocyetes spp.; Cercomeromorpha, inparticular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp.,Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp.,Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephalaspp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

As used herein, the term “animal” includes warm-blooded animals(including humans) and fish. Preferred are mammals, such as cattle,sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogsand cats, water buffalo, donkeys, fallow deer and reindeer, and also infurbearing animals such as mink, chinchilla and raccoon, birds such ashens, geese, turkeys and ducks and fish such as fresh- and salt-waterfish such as trout, carp and eels. Particularly preferred are domesticanimals, such as dogs or cats.

In general, “parasiticidally effective amount” means the amount ofactive ingredient needed to achieve an observable effect on growth,including the effects of necrosis, death, retardation, prevention, andremoval, destruction, or otherwise diminishing the occurrence andactivity of the target organism. The parasiticidally effective amountcan vary for the various compounds/compositions used in the invention. Aparasiticidally effective amount of the compositions will also varyaccording to the prevailing conditions such as desired parasiticidaleffect and duration, target species, mode of application, and the like.

Generally, it is favorable to apply the compounds of the presentinvention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably1 mg/kg to 50 mg/kg per day.

For oral administration to warm-blooded animals, the formula I compoundsmay be formulated as animal feeds, animal feed premixes, animal feedconcentrates, pills, solutions, pastes, suspensions, drenches, gels,tablets, boluses and capsules. In addition, the formula I compounds maybe administered to the animals in their drinking water. For oraladministration, the dosage form chosen should provide the animal with0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula Icompound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weightper day.

Alternatively, the formula I compounds may be administered to animalsparenterally, for example, by intraruminal, intramuscular, intravenousor subcutaneous injection. The formula I compounds may be dispersed ordissolved in a physiologically acceptable carrier for subcutaneousinjection. Alternatively, the formula I compounds may be formulated intoan implant for subcutaneous administration. In addition the formula Icompound may be transdermally administered to animals. For parenteraladministration, the dosage form chosen should provide the animal with0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula Icompound.

The formula I compounds may also be applied topically to the animals inthe form of dips, dusts, powders, collars, medallions, sprays, shampoos,spot-on and pour-on formulations and in ointments or oil-in-water orwater-in-oil emulsions. For topical application, dips and sprays usuallycontain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of theformula I compound. In addition, the formula I compounds may beformulated as ear tags for animals, particularly quadrupeds such ascattle and sheep.

Suitable preparations are:

-   -   Solutions such as oral solutions, concentrates for oral        administration after dilution, solutions for use on the skin or        in body cavities, pouring-on formulations, gels;    -   Emulsions and suspensions for oral or dermal administration;        semi-solid preparations;    -   Formulations wherein the active compound is processed in an        ointment base or in an oil-in-water or water-in-oil emulsion        base;    -   Solid preparations such as powders, premixes or concentrates,        granules, pellets, tablets, boluses, capsules; aerosols and        inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving theactive ingredient in a suitable solvent and optionally adding furtherauxiliaries such as acids, bases, buffer salts, preservatives, andsolubilizers. Suitable auxiliaries for injection solutions are known inthe art. The solutions are filtered and filled sterile.

Oral solutions are administered directly. Concentrates are administeredorally after prior dilution to the use concentration. Oral solutions andconcentrates are prepared according to the state of the art and asdescribed above for injection solutions, sterile procedures not beingnecessary.

Solutions for use on the skin are trickled on, spread on, rubbed in,sprinkled on or sprayed on. Solutions for use on the skin are preparedaccording to the state of the art and according to what is describedabove for injection solutions, sterile procedures not being necessary.

Gels are applied to or spread on the skin or introduced into bodycavities. Gels are prepared by treating solutions which have beenprepared as described in the case of the injection solutions withsufficient thickener that a clear material having an ointment-likeconsistency results. Suitable thickeners are known in the art.

Pour-on formulations are poured or sprayed onto limited areas of theskin, the active compound penetrating the skin and acting systemically.Pour-on formulations are prepared by dissolving, suspending oremulsifying the active compound in suitable skin-compatible solvents orsolvent mixtures. If appropriate, other auxiliaries such as colorants,bioabsorption-promoting substances, antioxidants, light stabilizers,adhesives are added. Suitable such auxiliaries are known in the art.

Emulsions can be administered orally, dermally or as injections.Emulsions are either of the water-in-oil type or of the oil-in-watertype. They are prepared by dissolving the active compound either in thehydrophobic or in the hydrophilic phase and homogenizing this with thesolvent of the other phase with the aid of suitable emulsifiers and, ifappropriate, other auxiliaries such as colorants, absorption-promotingsubstances, preservatives, antioxidants, light stabilizers,viscosity-enhancing substances. Suitable hydrophobic phases (oils),suitable hydrophilic phases, suitable emulsifiers, and suitable furtherauxiliaries for emulsions are known in the art.

Suspensions can be administered orally or topically/dermally. They areprepared by suspending the active compound in a suspending agent, ifappropriate with addition of other auxiliaries such as wetting agents,colorants, bioabsorption-promoting substances, preservatives,antioxidants, light stabilizers. Suitable suspending agents, andsuitable other auxiliaries for suspensions including wetting agents areknown in the art.

Semi-solid preparations can be administered orally ortopically/dermally. They differ from the suspensions and emulsionsdescribed above only by their higher viscosity.

For the production of solid preparations, the active compound is mixedwith suitable excipients, if appropriate with addition of auxiliaries,and brought into the desired form. Suitable auxiliaries for this purposeare known in the art.

The compositions which can be used in the invention can comprisegenerally from about 0.001 to 95% of the compound of the presentinvention.

Ready-to-use preparations contain the compounds acting againstparasites, preferably ectoparasites, in concentrations of 10 ppm to 80percent by weight, preferably from 0.1 to 65 percent by weight, morepreferably from 1 to 50 percent by weight, most preferably from 5 to 40percent by weight.

Preparations which are diluted before use contain the compounds actingagainst ectoparasites in concentrations of 0.5 to 90 percent by weight,preferably of 1 to 50 percent by weight.

Furthermore, the preparations comprise the compounds of formula Iagainst endoparasites in concentrations of 10 ppm to 2 percent byweight, preferably of 0.05 to 0.9 percent by weight, very particularlypreferably of 0.005 to 0.25 percent by weight.

Topical application may be conducted with compound-containing shapedarticles such as collars, medallions, ear tags, bands for fixing at bodyparts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which releasecompounds of the present invention in total amounts of 10 mg/kg to 300mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160mg/kg body weight of the treated animal in the course of three weeks.

EXAMPLES Preparation Examples

With appropriate modification of the starting materials, the proceduresas described in the preparation examples below were used to obtainfurther compounds of formula I. The compounds obtained in this mannerare listed in the table C that follows, together with physical data.

Compounds can be characterized e.g. by coupled High Performance LiquidChromatography/mass spectrometry (HPLC/MS), by ¹H-NMR and/or by theirmelting points.

Analytical HPLC—Method 1: Agilent Eclipse Plus C18, 50×4.6 mm, ID 5 μm;Elution: A=10 mM Amm. Formate (0.1% Formic Acid), B=Acetonitrile (0.1%Formic Acid), Flow=1.2 ml/min. at 30° C.; Gradient:=10% B to 100% B—3min, hold for 1 min, 1 min—10% B. Run Time=5.01 min.

Analytical HPLC—Method 2: Kinetex XB C18 1,7μ 50×2.1 mm; A=Water+0.1%TFA, B=Acetonitrile, Flow=0.8 ml/min—1.0 ml/min in 1.5 min. at 60° C.;Gradient:5% B to 100% B—1.5 min.

¹H-NMR: The signals are characterized by chemical shift (ppm, 6 [delta])vs. tetramethylsilane respectively, CDCl₃ for ¹³C-NMR, by theirmultiplicity and by their integral (relative number of hydrogen atomsgiven). The following abbreviations are used to characterize themultiplicity of the signals: m=multiplet, q=quartet, t=triplet,d=doublet and s=singlet.

Abbreviations used are: d for day(s), h for hour(s), min for minute(s),r.t./room temperature for 20-25° C., Rt for retention time; DMSO fordimethyl sulfoxide, OAc for acetate, EtOAc for ethyl acetate, EtOH forethanol, THF for tetrahydrofuran, DMF for N,N-Dimethylformamide, DCM fordichloromethane, ACN for acetonitrile, TEA for triethyl amine and t-BuOHfor tert-butanol.

Example C-11-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4(trifluoromethoxy)phenyl]carbamimidoyl]indazol-6-yl]methyleneamino]thiourea(C-1) Step 1: Synthesis of 6-bromo-3-iodo-1H-indazole

A mixture of 6-bromo-1H-indazole (1 g) and Potassium hydroxide (0.570 g)in DMF (15 mL) was stirred at 0° C. and Iodine (1.93 g) was added. Themixture was stirred at ambient temperature for 3 h and Sodiumthiosulphate solution (5% in water) was subsequently added. The mixturewas extracted with EtOAc and the extracts dried over anhydrous Sodiumsulphate and evaporated invacuo and the residue obtained was subjectedto silica gel flash column chromatography, eluting with a gradient ofEtOAc and Heptane to obtain the title compound as a white solid (1.5 g).HPLC/MS (method 1): Rt: 1.89 min; m/z=320.8 (M-1)+; ¹H NMR (500 MHz,DMSO-d6) δ 13.68 (s, 1H), 7.87 (s, 1H), 7.45 (d, J=8.6 Hz, 1H), 7.38 (d,J=8.6 Hz, 1H).

Step 2: Synthesis of 6-bromo-3-iodo-1-methyl-indazole

To a mixture of 6-bromo-3-iodo-1H-indazole (1.6 g) and Potassiumcarbonate (1.03 g) in THE (15 mL) was added Methyl iodide (0.84 g)drop-wise. The reaction mixture was subsequently diluted with water,extracted with EtOAc, the ethyl acetate extracts dried over sodiumsulphate and concentrated under reduced pressure. The resultant residuewas subjected to silica gel flash column chromatography eluting with agradient of EtOAc and Heptane to get the title compound as a off-whitesolid. (1.2 g). ¹H NMR (500 MHz, DMSO-d6) 8.04 (s, 1H), 7.39-7.29 (m,2H), 4.06 (s, 3H).

Step 3: Synthesis of 6-bromo-1-methyl-indazole-3-carbonitrile

To a nitrogen degassed solution of 6-bromo-3-iodo-1-methyl-indazole (0.1g) in DMF (4 mL) was added Zinc cyanide (0.040 g),(diphenylphosphino)ferrocene (0.008 g) andTris(dibenzylideneacetone)dipalladium(0) (0.016 g) and the mixture washeated at 60° C. for 3 h. The mixture was subsequently diluted withwater and extracted with EtOAc and the organic extracts dried overanhydrous sodium sulphate and evaporated invacuo. The resultant residuewas subjected to Silica gel flash column chromatography eluting with agradient of Ethyl acetate and Heptane to afford the title compound as ayellow solid (0.04 g). ¹H NMR (500 MHz, DMSOd6) δ 8.31 (dd, J=1.7, 0.7Hz, 1H), 7.86 (dd, J=8.7, 0.7 Hz, 1H), 7.55 (dd, J=8.7, 1.6 Hz, 1H),4.19 (s, 3H).

Step 4: Synthesis of 6-bromo-1-methyl-N-[4-(trifluoromethoxy) phenyl]indazole-3-carboxamidine

To a stirred solution of 6-bromo-1-methyl-indazole-3-carbonitrile (0.08g) in Toluene (3 mL) was added 4-(trifluoromethoxy)aniline (0.06 g) anda 2 M solution of Trimethyl aluminum in toluene (0.036 g). The mixturewas heated in a sealed tube at 90° C. for 2 h and subsequently cooled toambient temperature. A solution of Potassium hydroxide was addeddropwise and the mixture extracted with EtOAc. The organic extracts weredried over anhydrous Sodium sulphate, evaporated invacuo and theresultant solid was subjected to neutral Alumina flash columnchromatography, eluting with a gradient of EtOAc and Heptane to obtainthe title compound as a white solid. (0.04 g). HPLC/MS (method 1):Rt=1.67 min; m/z=413.10 (M+1)⁺; ¹H NMR (500 MHz, DMSO-d6) δ 8.27 (d,J=8.7 Hz, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.37 (dd, J=8.6, 1.6 Hz, 1H),7.30 (d, J=8.3 Hz, 2H), 7.04 (d, J=8.3 Hz, 2H), 6.34 (s, 2H), 4.12 (s,3H).

Step 5: Synthesis of1-methyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-indazole-3-carboxamidine

A solution of6-bromo-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(0.063 g) in 1,4-Dioxane (3 mL) was degassed with Nitrogen gas.Tri-n-butyl vinyl tin (0.073 g) and[1,1′-Bis(diphenylphosphino)ferrocene] dichloropalladium(II) (0.006 g)were subsequently added and the mixture heated at 100° C. for 2 h. Themixture was subsequently cooled to ambient temperature, diluted withwater and extracted with EtOAc. The organic layers were dried oversodium sulfate and concentrated under reduced pressure and resultantresidue subjected to Silica gel flash column chromatography eluting witha gradient of EtOAc/Heptane to get the title compound as a viscousliquid (0.035 g). HPLC/MS (method 1): Rt:1.590 min; m/z=361.40 (M+1)⁺.

Step 6: Synthesis of6-formyl-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine

To a stirred solution of1-methyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-indazole-3-carboxamidine(1.4 g) in 1,4-Dioxane (15 mL) was added a solution of Osmium tetroxide(0.050 g) in water (8 mL). The mixture was stirred for 12 h and Sodiumsulfite solution (0.5%) was subsequently added and the mixture extractedwith EtOAc. The organic extracts were dried over Sodium sulfate, and theresidue obtained was subjected to Silica gel flash column chromatographyeluting with a gradient of EtOAc and Heptane to obtain the titlecompound as viscous oil (0.65 g). HPLC/MS (method 1): Rt=1.413 min;m/z=363.40 (M+1)⁺; ¹H NMR (500 MHz, DMSO-d6) 10.17 (s, 1H), 8.50 (d,J=8.4 Hz, 1H), 8.41 (s, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.31 (d, J=8.3 Hz,2H), 7.06 (d, J=8.3 Hz, 2H), 6.40 (s, 2H), 4.24 (s, 3H).

Step 7: Synthesis of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]indazol-6-yl]methyleneamino]thiourea

A mixture of6-formyl-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(0.56 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.29 g) inAcetonitrile (7 mL) was heated at 80° C. for 2 h. The mixture was cooledto ambient temperature and the precipitated solids were filtered andsubjected to neutral Alumina column chromatography using a gradient ofDichloromethane and Methanol as eluent to afford the title compound as ayellow solid (0.260 g) HPLC/MS (method 1): Rt=1.76 min; m/z=554.25(M+1)⁺; ¹H NMR (500 MHz, DMSO-d6); δ 11.93 (s, 1H), 10.01 (s, 1H), 8.30(d, J=3.7 Hz, 2H), 8.13 (s, 1H), 7.91 (d, J=8.7 Hz, 1H), 7.44-7.17 (m,5H), 7.05 (d, J=8.4 Hz, 2H), 6.31 (s, 2H), 4.16 (s, 1H), 3.26-3.03 (m,1H), 1.20 (d, J=6.9 Hz, 6H).

Example C-26-[(E)-[(E)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(C-2)

A mixture of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-trifluoromethoxy)phenyl]carbamimidoyl]indazol-6-yl]methyleneamino]thiourea(0.20 g), Sodium acetate (0.06 g) and Methyl bromo acetate (0.066 g) inAcetonitrile (4 mL) was stirred at ambient temperature for 48 h. Thereaction mixture was subsequently diluted with water and extracted withEtOAc and the organic layer was dried over anhydrous Sodium sulphate andevaporated invacuo. The residue obtained was subjected to columnchromatography over neutral alumina, eluting with a gradient ofDichloromethane and Methanol to obtain the title compound as a yellowsolid (0.050 g).

HPLC/MS (method 1): Rt=1.73 min; m/z=594.35 (M+1)⁺; ¹H NMR (500 MHz,DMSO-d6); δ 8.45 (s, 1H), 8.41-8.27 (m, 1H), 7.98 (s, 1H), 7.74 (d,J=8.6 Hz, 1H), 7.50 (dt, J=15.1, 7.8 Hz, 2H), 7.42-7.19 (m, 4H), 7.09(s, 2H), 6.46 (s, 2H), 4.35-4.12 (m, 5H), 2.95-2.71 (m, 1H), 1.16 (dd,J=17.2, 6.8 Hz, 6H).

Example C-31-[(E)-[3-[(Z)—N,N′-dimethyl-N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]-1-methyl-indazol-6-yl]methyleneamino]-3-(2-isopropylphenyl)thiourea(C-3) Step 1: Synthesis of6-bromo-N,N′,1-trimethyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine

Sodium hydride (0.174 g) was added portion-wise to a stirred solution of6-bromo-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(1.2 g) in DMF (15 mL) at 0° C. Methyl iodide (1.65 g, 11.65 mmol) wassubsequently added. The mixture was stirred at ambient temperature for16 h and saturated ammonium chloride solution was added. The mixture wassubsequently extracted with EtOAc, the organic extracts dried overanhydrous Sodium sulfate and concentrated under reduced pressure. Theresidue obtained was subjected to flash column chromatography overneutral alumina, eluting with a gradient of Dichloromethane and Methanolto get the title compound as an off white solid (0.65 g). HPLC/MS(method 1): Rt=1.59 min; m/z=443.15 (M+1)⁺; ¹H NMR (500 MHz, DMSO-d6);7.96 (s, 1H), 7.32 (d, J=8.6 Hz, 1H), 7.23-7.12 (m, 1H), 6.86 (d, J=8.3Hz, 2H), 6.51 (d, J=8.4 Hz, 2H), 3.99 (s, 3H), 2.96 (s, 6H).

Step 2: Synthesis ofN,N′,1-trimethyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-indazole-3-carboxamidine

A mixture of6-bromo-N,N′,1-trimethyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidin(0.62 g), tri-butyl-vinyl tin (0.67 g) and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.052 g) in 1,4—Dioxane (15 mL) washeated at 100° C. for 12 h. The mixture was cooled to ambienttemperature, diluted with EtOAc and filtered through Celite. Thefiltrate was successively washed with water and a solution of Sodiumchloride and the organic layer was separated, dried over anhydrousSodium sulfate and concentrated under reduced pressure. The residueobtained was subjected to neutral Alumina column chromatography elutingwith a gradient of Ethyl acetate and Heptane to obtain the titlecompound as a viscous liquid (0.52 g). HPLC/MS (method 1): Rt=1.56 min;m/z=389.45 (M+1)⁺.

Step 3: Synthesis of6-formyl-N,N′,1-trimethyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine

To a stirred solution ofN,N′-1-trimethyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-indazole-3-carboxamidine (0.58 g) in 1,4-Dioxane (8 mL) was added a solution of Osmiumtetroxide (0.019 g) in water (4 mL), followed by the addition of Sodiumperiodate (1.0 g). The mixture was stirred for 12 h at ambienttemperature and a 0.5% solution of Sodium sulfite was added and themixture extracted with EtOAc. The organic extracts were dried overanhydrous Sodium sulphate and evaporated invacuo and the residueobtained was subjected to neutral Alumina column chromatography toobtain the title compound as a viscous liquid (0.27 g). HPLC/MS (method1): Rt=1.44 min; m/z=391.4 (M+1)⁺.

Step: 4 Synthesis of1-[(E)-[3-[(Z)—N,N′-dimethyl-N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]-1-methyl-indazol-6-yl]methyleneamino]-3-(2-isopropylphenyl)thiourea

A mixture of6-formyl-N,N′,1-trimethyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(0.25 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.134 g) in THE (4mL) was heated at 70° C. for 3 h. The mixture was concentrated underreduced and the residue obtained was purified by preparative HPLC toafford the title compound as a yellow solid (0.1 g). HPLC/MS (method 1):Rt=1.72 min; m/z=582.35 (M+1)⁺; ¹H NMR (500 MHz, DMSO-d6) δ 11.93 (s,1H), 10.0 (s, 1H), 8.21 (m, 1H), 8.10 (m, 1H), 7.98-7.96 (m, 1H),7.53-7.52 (m, 1H), 7.36-7.35 (m, 1H), 7.32-7.30 (m, 1H), 7.22-7.19 (m,2H), 7.17-7.15 (m, 2H), 7.05-7.04 (m, 2H), 4.13 (d, J=1.4 Hz, 3H), 3.50(s, 3H), 3.28 (s, 3H), 3.11-3.08 (m, 1H) 1.16-1.17 (m, 6H).

Example C-4[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[1-methyl-3-[methyl-[4-(trifluoromethoxy)phenyl]carbamothioyl]indazol-6-yl]carbamate(C-4)

A solution of[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[1-methyl-3-[methyl-[4-(trifluoromethoxy)phenyl]carbamoyl]indazol-6-yl]carbamate(0.070 g) Lawesson's reagent (0.072 g) in pyridine was heated at 110° C.for 16 h. The reaction was then allowed to cool to room temperature, theprecipitate was isolated by filtration and purified by columnreverse-phase chromatography eluting with a gradient ofacetonitrile/water to afford[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[1-methyl-3-[methyl-[4-(trifluoromethoxy)phenyl]carbamothioyl]indazol-6-yl]carbamate(47 mg). HPLC/MS (method 2): Rt=1.29 min; m/z=613 (M+); ¹H NMR (500 MHz,CDCl₃) δ 7.96 (d, J=8.7 Hz, 1H), 7.72 (s, 1H), 7.14-7.01 (m, 5H), 6.77(dd, J=8.7, 1.8 Hz, 1H), 6.18 (d, J=2.0 Hz, 1H), 5.30 (s, 1H), 3.95 (s,3H), 3.80-3.64 (m, 6H), 3.63-3.48 (m, 13H), 3.22 (t, J=9.5 Hz, 1H), 1.33(d, J=6.2 Hz, 4H).

Example C-51-[(E)-[3-[(Z)—N-(4-hydroxyphenyl)-N′-methoxy-carbamimidoyl]-1-methyl-indazol-6-yl]methyleneamino]-3-(2-isopropylphenyl)thiourea(C-5) Step 1: Synthesis of 6-bromo-1H-indazole-3-carbaldehyde

To the stirring solution of 6-bromo-1H-indole (10 g) in Acetone (200mL), was added solution of Sodium nitrite (28.155g) in Water (50 mL) at0° C. Mixture was stirred for 10 min and 2N HCl (120 mL) was addeddropwise by dropping funnel at 0°. Mixture was continued to stir for 1h. The reaction mixture was concentrated and the solid was filtered. Thesolid was washed with cold acetone (20 mL) and dried under vacuum toafford 6-bromo-1H-indazole-3-carbaldehyde as brown solid (5.5 g).HPLC/MS (method 1): Rt=2.2 min, m/z=225 (M+); ¹H NMR (500 MHz, DMSO-d6)δ 14.28 (s, 1H), 10.19 (s, 1H), 8.08 (d, J=8.5 Hz, 1H), 7.97 (d, J=1.5Hz, 1H), 7.51 (dd, J=8.6, 1.7 Hz, 1H).

Step 2: Synthesis of 6-bromo-1-methyl-indazole-3-carbaldehyde

To the stirring solution of 6-bromo-1H-indazole-3-carbaldehyde (3.1 g)in dry THE (30 mL), were added Methyl iodide (2.94 g) and Potassiumcarbonate (3.9 g) at room temperature under inert atmosphere. Thereaction mixture was continued to stir for 12 h at room temperature.Reaction mixture was diluted with ethyl acetate and washed with water.The mixture was concentrated under reduced pressure and the residueobtained was purified by column chromatography eluting with a gradientof Ethyl acetate and Heptane to afford the title compound (2.3 g). ¹HNMR (300 MHz, DMSO-d6) δ 13.17 (s, 1H), 8.14 (d, J=1.5 Hz, 1H), 7.99(dd, J=8.7, 0.7 Hz, 1H), 7.45 (dd, J=8.6, 1.6 Hz, 1H).

Step 3: Synthesis of 6-bromo-1-methyl-indazole-3-carboxylic acid

To the stirring solution of 6-bromo-1-methyl-indazole-3-carbaldehyde(3.5 g) in ACN (30 mL) and Water (10 mL), was added Potassiumpermanganate (3.4 g) at room temperature under inert atmosphere.Reaction was continued for 12 h at room temperature. Reaction mixturewas diluted with water and filtered through a celite bed. The filtratepH was adjusted up to ˜2-3 using 1N HCl. Precipitated product wasfiltered through a filter paper and dried under reduced pressure toafford the title compound (2.3 g). HPLC/MS (method 1): Rt=1.56 min;m/z=255 (M+); ¹H NMR (300 MHz, DMSO-d6) δ 8.14 (d, J=1.5 Hz, 1H), 7.99(dd, J=8.7, 0.7 Hz, 1H), 7.45 (dd, J=8.6, 1.6 Hz, 1H), 4.13 (s, 3H).

Step 4: Synthesis of6-bromo-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamide

To the stirring solution of 6-bromo-1-methyl-indazole-3-carboxylic acid(0.3 g) in DCM (5 mL) was added TEA (0.39 g) and para-trifluoro methoxyaniline (0.208 g). Reaction mixture was stirred for 5 min andPropylphosphonic anhydride (50% in EtOAc, 2.24 ml) was added. Mixturewas stirred for 16 h at room temperature. Reaction mixture was dilutedwith DCM and washed with water. The mixture was concentrated underreduced pressure and the residue obtained was purified by columnchromatography eluting with a gradient of Ethyl acetate and Heptane toafford the title compound (0.280 mg). HPLC/MS (method 1): Rt=2.233 min;m/z=414 (M+); ¹H NMR (500 MHz, DMSO-d6) δ 10.65 (s, 1H), 8.19 (s, 1H),8.15 (d, J=8.6 Hz, 1H), 8.01 (d, J=8.9 Hz, 2H), 7.48 (d, J=8.6 Hz, 1H),7.37 (d, J=8.6 Hz, 2H), 4.20 (s, 3H).

Step 5: Synthesis of6-bromo-N′-hydroxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine

6-bromo-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamide (2g) was heated in SOCl₂ (6 mL) at 120° C. for 16 h. After completion thereaction mixture was concentrated and dried under vacuum. To the residueEtOH (20 mL) was added and cooled to 0° C. TEA (1.95 g) and Hydroxylamine hydrochloride (1 g) was added and heated at 90° C. for 2-4 h.Reaction mixture was quenched with brine and extracted with EtOAc. Themixture was concentrated under reduced pressure and the residue obtainedwas purified by column chromatography eluting with a gradient of Ethylacetate and Heptane to afford the title compound (1.6 g). HPLC/MS(method 1): Rt=1.94 min; m/z=431(M+1); ¹H NMR (500 MHz, DMSO-d6) δ 10.89(s, 1H), 8.60 (s, 1H), 8.03 (d, J=1.5 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H),7.32 (m, 1H) 7.07 (d, J=8.6 Hz, 2H), 6.74 (d, J=9.0 Hz, 2H), 3.99 (s,3H).

Step 6: Synthesis of6-bromo-N′-methoxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine

To the stirring solution of6-bromo-N′-hydroxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(1.5 g) in DMF (10 mL) was added Potassium carbonate (1.28 g) and Methyliodide (0.527 g). Reaction mixture was stirred for 4 h at roomtemperature. The reaction mixture was quenched with cold water and solidwas filtered. Solid was dissolved in EtOAc, washed with brine, driedover anhydrous sodium sulphate and filtered. The filtrate wasconcentrated under reduced pressure and the residue obtained waspurified by column chromatography eluting with a gradient of Ethylacetate and Heptane to afford the title compound (0.04 g). ¹H NMR (500MHz, DMSO-d6) δ 8.83 (s, 1H), 8.04 (dd, J=1.7, 0.6 Hz, 1H), 7.82 (dd,J=8.7, 0.6 Hz, 1H), 7.33 (dd, J=8.6, 1.6 Hz, 1H), 7.14-7.00 (m, 2H),6.77 (d, J=9.0 Hz, 2H), 4.00 (s, 3H), 3.91 (s, 3H).

Step 7: Synthesis ofN′-methoxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-indazole-3-carboxamidine

To the stirring solution of6-bromo-N′-methoxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine (0.25 g) in Toluene (5 mL), was added[1,1′-Bis(diphenylphosphino) ferrocene] dichloropalladium(II) (0.025 g).N₂ gas was purged to the mixture for 5 min. Ethyl-tributyl-tin (0.268 g)was added and heated at 110° C. for 4 h. Reaction mixture was quenchedwith brine and extracted with EtOAc. The mixture was concentrated underreduced pressure and the residue obtained was purified by columnchromatography eluting with a gradient of Ethyl acetate and Heptane toafford the title compound (0.170 g). HPLC/MS (method 1): Rt=2.299 min;m/z=391 (M+1); ¹H NMR (500 MHz, DMSO-d6) δ 8.80 (s, 1H), 7.80 (d, J=8.5Hz, 1H), 7.71 (s, 1H), 7.38 (dd, J=8.5, 1.3 Hz, 1H), 7.11-7.05 (m, 2H),6.88 (dd, J=17.6, 10.9 Hz, 1H), 6.81-6.75 (m, 2H), 5.98 (dd, J=17.6, 1.0Hz, 1H), 5.40-5.34 (m, 1H), 4.02 (s, 3H), 3.9 (s, 3H).

Step 8: Synthesis of6-formyl-N′-methoxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine

To the stirring solution ofN′-methoxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-indazole-3-carboxamidine(0.07g) in Dioxane (2 mL) and Water (1 mL), was added Osmium tetraoxide(0.001 g) and Sodium periodate (0.095 g) at 0° C. Reaction mixture wascontinued to stir at 0° C. to room temperature for 2 h. Reaction mixturewas quenched with brine and extracted with EtOAc. The mixture wasconcentrated under reduced pressure and the residue obtained waspurified by column chromatography eluting with a gradient of Ethylacetate and Heptane to afford the title compound (0.04 g). HPLC/MS(method 1): Rt=1.99 min, m/z=391 (M−); ¹H NMR (500 MHz, DMSO-d6) δ 10.12(s, 1H), 8.88 (s, 1H), 8.35 (s, 1H), 8.01 (d, J=8.5 Hz, 1H), 7.66 (dd,J=8.5, 1.1 Hz, 1H), 7.07 (d, J=8.7 Hz, 2H), 6.79-6.73 (m, 2H), 4.11 (s,3H), 3.91 (s, 3H).

Step 9: Synthesis of1-(2-isopropylphenyl)-3-[(E)-[3-[(Z)—N′-methoxy-N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]-1-methyl-indazol-6-yl]methyleneamino]thiourea

To the stirring solution of6-formyl-N′-methoxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(0.16 g) in EtOH (2 mL), was added semi carbazide (0.085 g) and heatedat 90° C. for 3 h. The mixture was concentrated under reduced pressureand the residue obtained was purified by column chromatography elutingwith a gradient of Ethyl acetate and Heptane to afford the titlecompound (0.08 g). HPLC/MS (method 1): Rt=2.24 min; m/z=584 (M+); ¹H NMR(500 MHz, DMSO-d6) δ 11.92 (s, 1H), 10.00 (s, 1H), 8.84 (s, 1H), 8.27(s, 1H), 8.05 (s, 1H), 7.91 (d, J=8.6 Hz, 1H), 7.80 (d, J=8.6 Hz, 1H),7.40-7.28 (m, 2H), 7.24 (d, J=4.1 Hz, 2H), 7.08 (d, J=8.5 Hz, 2H),6.81-6.75 (m, 2H), 4.06 (s, 3H), 3.91 (s, 3H), 3.14 (p, J=6.9 Hz, 1H),1.20 (d, J=6.8 Hz, 6H).

Example C-66-[(E)-[(Z)-[3-(2-isopropylphenyl)-5-oxo-thiazolidin-2-ylidene]hydrazono]methyl]-N′-methoxy-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(C-6)

To the stirring solution of1-(2-isopropylphenyl)-3-[(E)-[3-[(Z)—N′-methoxy-N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]-1-methyl-indazol-6-yl]methyleneamino]thiourea (0.12 g) inEtOH (2 mL), was added Sodium acetate (0.037 g) and Methyl bromo acetate(0.035 g).

Reaction mixture was stirred for 16 h at room temperature. Reactionmixture was diluted with EtOAc and washed with water. The mixture wasconcentrated under reduced pressure and the residue obtained waspurified by column chromatography eluting with a gradient of Ethylacetate and Heptane to afford the title compound (0.05 g). HPLC/MS(method 1): Rt=2.29 min; m/z=624 (M+); ¹H NMR (500 MHz, DMSO-d6) δ 8.84(s, 1H), 8.42 (s, 1H), 7.95-7.89 (m, 2H), 7.68 (d, J=8.5 Hz, 1H),7.56-7.43 (m, 2H), 7.35 (td, J=7.6, 1.6 Hz, 1H), 7.32-7.24 (m, 1H), 7.08(d, J=8.6 Hz, 2H), 6.82-6.73 (m, 2H), 4.34-4.10 (m, 2H), 4.02 (s, 3H),3.92 (s, 3H), 2.80 (p, J=6.9 Hz, 1H), 1.16 (dd, J=15.0, 6.8 Hz, 6H).

Example 20 Synthesis of6-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]-N′[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine(C-20) Step-1: Synthesis of 6-bromo-1,2-benzothiazole-3-carbonitrile

To a stirred solution of 6-bromo-1,2-benzothiazole-3-carboxamide (4.5 g)in Phosphoryl chloride (45 mL) was heated at 120° C. for 3 h. Aftercompletion of the reaction Phosphoryl chloride was removed under reducedpressure, crude was dissolved in water (50 mL). The mixture wasextracted with EtOAc and the extracts were dried over anhydrous sodiumsulphate and evaporated invacuo and the residue obtained was subjectedto silica gel flash column chromatography, eluting with a gradient ofEtOAc and Heptane to obtain the title compound (2.8 g).

Step-2: Synthesis of6-bromo-N′-[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine

To a stirred solution of 6-bromo-1,2-benzothiazole-3-carbonitrile (3.4g) in Toluene (35.0 mL) was added 4-(trifluoromethoxy)aniline (3.023 g)and a (2 M) solution of Trimethyl aluminum in Toluene (14.22 mL). Themixture was heated at 110° C. for 16 h and subsequently cooled toambient temperature. A solution of Potassium hydroxide was addeddropwise and the mixture extracted with EtOAc. The organic extracts wasdried over anhydrous sodium sulphate, evaporated invacuo and theresultant solid was subjected to silica gel flash column chromatography,eluting with a gradient of EtOAc and Heptane to obtain the titlecompound (5.0 g). HPLC/MS (method 1): Rt=2.32 min; m/z=417.10 (M+2)⁺.

Step-3: Synthesis ofN′-[4-(trifluoromethoxy)phenyl]-6-vinyl-1,2-benzothiazole-3-carboxamidine

A solution of6-bromo-N′-[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine(1.1 g) in Toulene (15 mL) was degassed with Nitrogen gas. Tri-n-butylvinyl tin (1.25 mL) and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.110 g) were subsequently added and the mixtureheated at 110° C. for 4 h. The mixture was subsequently cooled toambient temperature, diluted with water and extracted with EtOAc. Theorganic extracts were dried over sodium sulfate and concentrated underreduced pressure and resultant residue subjected to silica gel flashcolumn chromatography eluting with a gradient of EtOAc and Heptane toget the title compound (0.800 g). HPLC/MS (method 1): Rt=2.21 min;m/z=364 (M+1)⁺.

Step-4: Synthesis of6-formyl-N′-[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine

To a stirred solution ofN′-[4-(trifluoromethoxy)phenyl]-6-vinyl-1,2-benzothiazole-3-carboxamidine(1.0 g) in 1,4-Dioxane (6.0 mL) were added a solution of Osmiumtetroxide (0.021 g) in Water (4.0 mL), Sodium periodate (1.29 g). Themixture was stirred for 4 h and Sodium sulfite solution (0.5%) wassubsequently added and the mixture extracted with EtOAc. The organicextracts were dried over sodium sulfate, and the residue obtained wassubjected to silica gel flash column chromatography eluting with agradient of EtOAc and Heptane to obtain the title compound (0.500 g).HPLC/MS (method 1): Rt=1.972 min; m/z=366 (M+1)+;

Step-5: Synthesis of1-(2-isopropylphenyl)-3-[(E)-[3-[(Z)—N′-[4-(trifluoromethoxy)phenyl]carbamimidoyl]-1,2-benzothiazol-6-yl]methyleneamino]thiourea

A mixture of6-formyl-N′-[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine(0.250 g), 1-amino-3-(2-isopropylphenyl)thiourea (0.143 g) in Aceticacid (2.0 mL) was stirred at ambient temperature for 2 h. The reactionmixture was dissolved in Water (50 mL). The mixture was extracted withEtOAc and the extracts dried over anhydrous sodium sulphate andevaporated invacuo and the residue obtained was subjected to silica gelflash column chromatography, eluting with a gradient of EtOAc andHeptane to obtain the title compound (0.230 g) HPLC/MS (method 1) Rt:2.24 min; m/z=557 (M+1)⁺; ¹H NMR (300 MHz, DMSOd6) δ 12.00 (s, 1H),10.11 (s, 1H), 9.00 (d, J=8.7 Hz, 1H), 8.70 (s, 1H), 8.30 (s, 1H), 8.18(dd, J=8.8, 1.4 Hz, 1H), 7.42-7.29 (m, 4H), 7.29-7.17 (m, 2H), 7.10 (d,J=8.3 Hz, 2H), 6.73 (s, 2H), 3.14 (p, J=6.8 Hz, 1H), 1.19 (d, J=6.9 Hz,6H).

Example 21 Synthesis of6-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]-N′[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine(C-21)

A mixture of1-(2-isopropylphenyl)-3-[(E)-[3-[(Z)—N′-[4-(trifluoromethoxy)phenyl]carbamimidoyl]-1,2-benzothiazol-6-yl]methyleneamino]thiourea(0.230 g), Methyl bromo acetate (0.95 g) in EtOH (10 mL), was addedSodium acetate (0.051 g) at 0° C. The mixture was stirred at ambienttemperature for 16 h. Water (50 mL) was subsequently added. The mixturewas extracted with EtOAc and the organic extracts were dried overanhydrous sodium sulphate and evaporated invacuo and the residueobtained was subjected to silica gel flash column chromatography,eluting with a gradient of EtOAc and heptane to obtain the titlecompound (0.080 g). HPLC/MS (method 1): Rt: 2.29 min; m/z=597 (M+1)⁺; ¹HNMR (300 MHz, DMSO-d6) δ 9.06 (d, J=8.7 Hz, 1H), 8.51 (d, J=14.5 Hz,2H), 7.95 (d, J=8.7 Hz, 1H), 7.57-7.42 (m, 2H), 7.41-7.23 (m, 4H), 7.10(d, J=8.7 Hz, 2H), 6.73 (s, 2H), 4.35-4.04 (m, 2H), 2.80 (p, J=6.7 Hz,1H), 1.15 (dd, J=8.9, 6.8 Hz, 6H).

Example C-241-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[(E)-[4-(trifluoromethoxy)phenyl]iminomethyl]indazol-6-yl]methyleneamino]thiourea(C-24) Step 1: Synthesis of Methyl 3-formyl-1H-indazole-6-carboxylate

To the stirring solution of Methyl 1H-indole-6-carboxylate (5 g) inAcetone (100 mL), was added solution of Sodium nitrite (15.75 g) inwater (27 mL) at 0° C. Mixture was stirred for 10 min and 2N HCl (64 mL)was added dropwise by dropping funnel at 0° C. Mixture was continued tostir for 12 h. The reaction mixture was concentrated and the solid wasfiltered. The solid was washed with cold acetone (20 mL) and dried undervacuum to afford title compound as solid (5 g). HPLC/MS (method 1):Rt=1.483 min, m/z=203.4 (M+1)⁺.

Step 2: Synthesis of Methyl 3-formyl-1-methyl-indazole-6-carboxylate

To the stirring solution of Methyl 3-formyl-1H-indazole-6-carboxylate(3.9 g) in dry THE (39 mL), were added Methyl iodide (4.067 g) andPotassium carbonate (5.28 g) at room temperature under inert atmosphere.The reaction mixture was continued to stir for 12 h at room temperature.Reaction mixture was diluted with EtOAc and washed with water. Theorganic layers were dried over Sodium sulfate and concentrated underreduced pressure and resultant residue subjected to Silica gel flashcolumn chromatography eluting with a gradient of EtOAc/Heptane to affordthe title compound (3 g). HPLC/MS (method 1): Rt=1.648 min, m/z=217.90(M+1)⁺.

Step 3: Synthesis of Methyl3-(1,3-dioxolan-2-yl)-1-methyl-indazole-6-carboxylate

To the stirring solution of Methyl3-formyl-1-methyl-indazole-6-carboxylate (3 g) in Toluene (30 mL), wereadded p-Toluenesulfonic acid (0.262 g) and Ethelene glycol (2.56 g) atroom temperature under inert atmosphere. Reaction was continued to stirat 105° C. for 12 h. Reaction mixture was diluted with EtOAc and washedwith aqeuous sodium bicarbonate solution. The organic layers were driedover Sodium sulfate and concentrated under reduced pressure andresultant residue subjected to Silica gel flash column chromatographyeluting with a gradient of EtOAc/Heptane to afford the title compound(1.5 g). HPLC/MS (method 1): Rt=1.590 min, m/z=262.85 (M+1)⁺.

Step 4: Synthesis of[3-(1,3-dioxolan-2-yl)-1-methyl-indazol-6-yl]methanol

To the stirring solution of Methyl3-(1,3-dioxolan-2-yl)-1-methyl-indazole-6-carboxylate (1.5 g) in DCM (15mL), was added DIBAL-H (1.79 g) and mixture was stirred at −78° C. for 2h. Reaction mixture was quenched with aqueous sodium bicarbonatesolution and extracted with DCM. The organic layers were dried overSodium sulfate and concentrated under reduced pressure and resultantresidue subjected to Silica gel flash column chromatography eluting witha gradient of EtOAc/Heptane to afford the title compound (1.5 g).

HPLC/MS (method 1): Rt=1.204 min, m/z=234.85 (M+1)⁺.

Step 5: Synthesis of3-(1,3-dioxolan-2-yl)-1-methyl-indazole-6-carbaldehyde

To a stirring solution of[3-(1,3-dioxolan-2-yl)-1-methyl-indazol-6-yl]methanol (1.5 g) in dry DCM(15 mL), were added Dess Martin Periodinane (2.715 g) and Sodiumbicarbonate (0.538 g) at room temperature under inert atmosphere. Thereaction mixture was continued to stir for 12 h at room temperature.Reaction mixture was diluted with DCM and washed with water. The organiclayers were dried over Sodium sulfate and concentrated under reducedpressure and resultant residue subjected to Silica gel flash columnchromatography eluting with a gradient of EtOAc/Heptane to afford thetitle compound (0.9 g). HPLC/MS (method 1): Rt=1.458 min, m/z=232.9(M+1)⁺.

Step 6: Synthesis of1-[(E)-[3-(1,3-dioxolan-2-yl)-1-methyl-indazol-6-yl]methyleneamino]-3-(2-isopropylphenyl)thiourea

To the stirring solution of3-(1,3-dioxolan-2-yl)-1-methyl-indazole-6-carbaldehyde (0.85 g) in EtOH(10 mL), was added 1-amino-3-(2-isopropylphenyl)thiourea (0.766 g) andmixture was stirred at 85° C. for 3 h. The precipitated product wasfiltered though a paper and dried under reduced pressure to afford thetitle compound (1.4 g). HPLC/MS (method 1): Rt=1.939 min, m/z=424(M+1)⁺.

Step 7: Synthesis of1-[(E)-(3-formyl-1-methyl-indazol-6-yl)methyleneamino]-3-(2-isopropylphenyl)thiourea

To the stirring solution of1-[(E)-[3-(1,3-dioxolan-2-yl)-1-methyl-indazol-6-yl]methyleneamino]-3-(2-isopropylphenyl)thiourea(1.4 g) in Acetone (14 mL) was added p-Toluenesulfonic acid (0.063 g)room temperature under inert atmosphere. Reaction mixture was stirredfor 12 h at room temperature. Reaction mixture was neutralised withaqueous sodium bicarbonate solution and extracted with EtOAc. Theorganic layers were dried over Sodium sulfate and concentrated underreduced pressure and resultant residue subjected to Silica gel flashcolumn chromatography eluting with a gradient of EtOAc/Heptane to affordthe title compound (0.9 g).

HPLC/MS (method 1): Rt=1.931 min, m/z=379.9 (M+1)⁺.

Step 8: Synthesis of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[(E)-[4-(trifluoromethoxy)phenyl]iminomethyl]indazol-6-yl]methyleneamino]thiourea

To the stirring solution of1-[(E)-(3-formyl-1-methyl-indazol-6-yl)methyleneamino]-3-(2-isopropylphenyl)thiourea(0.65 g) in Ethanol (7 mL) were added 4-(Trifluoromethoxy)aniline (0.334g) and Acetic acid (2-3 drops) at room temperature under inertatmosphere. The reaction mixture was continued to stir at 85° C. for 3h. The mixture was concentrated under reduced pressure and the residueobtained was purified by column chromatography eluting with a gradientof Ethyl acetate and Heptane to afford the title compound (0.2 g).HPLC/MS (method 1): Rt=2.338 min; m/z=537 (M+1)⁺.

Example C-25(2Z)-3-(2-isopropylphenyl)-2-[(E)-[1-methyl-3-[(E)-[4-(trifluoromethoxy)phenyl]iminomethyl]indazol-6-yl]methylenehydrazono]thiazolidin-4-one(C-25)

To the stirring solution of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[(E)-[4-(trifluoromethoxy)phenyl]iminomethyl]indazol-6-yl]methyleneamino]thiourea (0.3 g) in EtOH(6 mL), were added Sodium acetate (0.092 g) and Methyl-2-bromoacetate(0.102 g). Reaction mixture was stirred for 12 h at room temperature.Reaction mixture was diluted with ethyl acetate and washed with water.The organic layers were dried over Sodium sulfate and concentrated underreduced pressure and resultant residue subjected to Silica gel flashcolumn chromatography eluting with a gradient of EtOAc/Heptane to affordthe title compound (0.07 g). HPLC/MS (method 1): Rt=2.379 min;m/z=578.85 (M+1)⁺; ¹H NMR (300 MHz, DMSO-d6) δ 8.87 (s, 1H), 8.47 (s,1H), 8.43 (d, J=8.5 Hz, 1H), 8.02 (s, 1H), 7.83 (d, J=8.3 Hz, 1H),7.55-7.40 (m, 6H), 7.31 (dd, J=17.7, 7.2 Hz, 2H), 4.40-4.04 (m, 5H),2.7-2.9 (m, 1H), 1.16 (dd, J=10.3, 6.8 Hz, 6H).

Example C-261-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]pyrazolo[3,4-b]pyridin-6-yl]methyleneamino]thiourea(C-26) Step 1: Synthesis of6-chloro-1-methyl-3-vinyl-pyrazolo[3,4-b]pyridine

A solution of 6-chloro-3-iodo-1-methyl-pyrazolo[3,4-b]pyridine (3.8 g)in 1,4-Dioxane (50 mL) was degassed with Nitrogen gas. Tri-n-butyl vinyltin (4.925 g) and Bis(triphenylphosphine)palladium(II) dichloride (0.454g) were subsequently added and the mixture heated at 100° C. for 3 h.The mixture was subsequently cooled to ambient temperature, diluted withwater and extracted with EtOAc. The organic layers were dried overSodium sulfate and concentrated under reduced pressure and resultantresidue subjected to Silica gel flash column chromatography eluting witha gradient of EtOAc/Heptane to get the title compound (1.6 g). ¹H NMR(300 MHz, Chloroform-d) δ 8.15 (d, J=8.4 Hz, 1H), 7.23 (s, 2H), 7.15 (d,J=8.4 Hz, 1H), 6.94 (dd, J=18.0, 11.4 Hz, 1H), 6.03 (dd, J=18.0, 0.9 Hz,1H), 5.56 (dd, J=11.4, 0.9 Hz, 1H), 4.10 (s, 3H).

Step 2: Synthesis of6-chloro-1-methyl-pyrazolo[3,4-b]pyridine-3-carbaldehyde

To a stirred solution of6-chloro-1-methyl-3-vinyl-pyrazolo[3,4-b]pyridine (3.6 g) in 1,4-Dioxane(100 mL) was added a solution of Osmium tetroxide (0.236 g) in water (70mL). To this solution Sodium periodate (7.957 g) was added in portionand the mixture was stirred for 12 h at room temperature. Sodium sulfitesolution (0.5%) was subsequently added and the mixture extracted withEtOAc. The organic extracts were dried over Sodium sulfate, and theresidue obtained was subjected to Silica gel flash column chromatographyeluting with a gradient of EtOAc/Heptane to obtain the title compound(3.4 g). HPLC/MS (method 1): ¹H NMR (300 MHz, DMSO-d6) δ 10.11 (s, 1H),8.55 (d, J=8.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 4.18 (s, 3H).

Step 3: Synthesis of6-chloro-1-methyl-pyrazolo[3,4-b]pyridine-3-carbonitrile

To a stirred solution of6-chloro-1-methyl-pyrazolo[3,4-b]pyridine-3-carbaldehyde in acetonitrilewas added Triethylamine (20 mL) and Hydroxylamine hydrochloride (1.25 g)and the mixture was heated at 65° C. for 3 h. After the startingmaterial was consumed, the reaction mixture was cooled to 0° C. thenmore Triethylamine (6 mL) was added to it followed by dropwise additionof Trifluoroacetic anhydride (10 mL) maintaining the temperature at 0°C. The reaction mixture was stirred at room temperature for 3 h and thenwas poured into an ice-water under stirring. The precipitated solid wasfiltered, washed with water and dried to obtain the title compound (2.2g).

HPLC/MS (method 1): Rt=1.553 min; m/z=No Ionization; 1H NMR (300 MHz,DMSO-d6) δ 8.53 (d, J=8.5 Hz, 1H), 7.57 (d, J=8.5 Hz, 1H), 4.15 (s, 3H).

Step 4:6-chloro-1-methyl-N-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-b]pyridine-3-carboxamidine

To a stirred solution of6-chloro-1-methyl-pyrazolo[3,4-b]pyridine-3-carbonitrile (1.9 g) inToluene (40 mL) was added 4-(trifluoromethoxy)aniline (1.747 g) and a 2M solution of Trimethyl aluminum in toluene (0.923 g). The mixture washeated in a sealed tube at 90° C. for 4 h and subsequently cooled toambient temperature. A solution of Potassium hydroxide was addeddropwise and the mixture was extracted with EtOAc. The organic extractswere dried over anhydrous Sodium sulphate, evaporated in vacuo and theresultant solid was subjected to neutral Alumina flash columnchromatography, eluting with a gradient of EtOAc/Heptane to obtain thetitle compound (2.4 g). HPLC/MS (method 1): Rt=1.618 min; m/z=370.95(M+1)⁺.

Step 5:1-methyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-pyrazolo[3,4-b]pyridine-3-carboxamidine

A solution6-chloro-1-methyl-N-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-b]pyridine-3-carboxamidine(1.3 g) in 1,4-Dioxane (20 mL) was degassed with Nitrogen gas.Tri-n-butyl vinyl tin (1.445 g) and[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.128 g)were subsequently added and the mixture was heated at 100° C. for 4 h.The mixture was subsequently cooled to ambient temperature, diluted withwater and extracted with EtOAc. The organic layers were dried overSodium sulfate and concentrated under reduced pressure and resultantresidue subjected to Silica gel flash column chromatography eluting witha gradient of EtOAc/Heptane to get the title compound (0.85 g). HPLC/MS(method 1): Rt:1.516 min; m/z=362.25 (M)⁺.

Step 6: Synthesis of6-formyl-1-methyl-N-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-b]pyridine-3-carboxamidine

To a stirred solution of1-methyl-N-[4-(trifluoromethoxy)phenyl]-6-vinyl-pyrazolo[3,4-b]pyridine-3-carboxamidine(0.8 g) in 1,4-Dioxane (10 mL) was added a solution of Osmium tetroxide(0.028 g) in water (8 mL). To this solution Sodium periodate (0.951 g)was added in portion and the mixture was stirred for 12 h at roomtemperature and Sodium sulfite solution (0.5%) was subsequently addedand the mixture was extracted with EtOAc. The organic extracts weredried over Sodium sulfate, and the residue obtained was subjected toSilica gel flash column chromatography eluting with a gradient ofEtOAc/Heptane to obtain the title compound (0.56 g).

HPLC/MS (method 1): Rt=1.396 min; m/z=362.95 (M+1)⁺.

Step 7: Synthesis of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]pyrazolo[3,4-b]pyridin-6-yl]methyleneamino]thiourea

A mixture of6-formyl-1-methyl-N-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-b]pyridine-3-carboxamidine(0.56 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.32 g) in Aceticacid (7 mL) was stirred at room temperature for 2 h. The mixture waspoured into an ice-water and the precipitated solids were filtered andwashed with water and dried to afford the title compound (0.260 g).HPLC/MS (method 1): Rt=1.76 min; m/z=555.30 (M+1)⁺; ¹H NMR (300 MHz,DMSO-d6) δ 12.16 (s, 1H), 10.26 (s, 1H), 8.58 (d, J=8.6 Hz, 1H), 8.42(d, J=8.6 Hz, 1H), 8.28 (s, 1H), 7.47-7.17 (m, 6H), 7.05 (d, J=8.3 Hz,2H), 6.43 (s, 2H), 4.16 (s, 3H), 3.18-3.03 (m, 1H), 1.19 (d, J=6.8 Hz,6H).

Example C-276-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]-1-methyl-N-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-b]pyridine-3-carboxamidine(C-27)

A mixture of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]carbamimidoyl] pyrazolo[3,4-b]pyridin-6-yl]methyleneamino]thiourea (0.30g), Sodium acetate (0.18 g) and Methyl bromo acetate (0.33 g) inAcetonitrile (6 mL) was stirred at ambient temperature for 48 h. Thereaction mixture was subsequently diluted with water and extracted withEtOAc and the organic layer was dried over anhydrous Sodium sulphate andevaporated invacuo. The residue obtained was subjected to columnchromatography over neutral alumina, eluting with a gradient ofDichloromethane and Methanol to obtain the title compound (0.170 g).HPLC/MS (method 1): Rt=1.91 min; m/z=595.10 (M+1)⁺; ¹H NMR (300 MHz,DMSO-d6) δ 8.73 (d, J=8.4 Hz, 1H), 8.26 (s, 1H), 7.95 (d, J=8.5 Hz, 1H),7.62-7.41 (m, 2H), 7.32 (q, J=7.8, 7.4 Hz, 4H), 7.07 (d, J=8.2 Hz, 2H),6.51 (s, 2H), 4.44-4.13 (m, 5H), 2.88-2.67 (m, 1H), 1.16 (dd, J=12.2,6.8 Hz, 6H).

Example C-28 Synthesis of6-[(E)-[(2Z)-2-(2-isopropylphenyl)imino-4-oxo-thiazolidin-3-yl]iminomethyl]-N′-[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine(C-28)

A mixture of6-formyl-N′-[4-(trifluoromethoxy)phenyl]-1,2-benzothiazole-3-carboxamidine(0.200 g), (2E)-3-amino-2-(2-isopropylphenyl)imino-thiazolidin-4-one(0.164 g) in Acetic acid (3 mL) was stirred at ambient temperature for 2h. Water (50 mL) was subsequently added. The mixture was extracted withEtOAc and the extracts was dried over anhydrous sodium sulphate andevaporated invacuo and the residue obtained was subjected to silica gelflash column chromatography, eluting with a gradient of EtOAc andHeptane to obtain the title compound as a solid (0.150 g) HPLC/MS(method 1) Rt: 2.36 min; m/z=596.8 (M)⁺; ¹H NMR (300 MHz, DMSO-d6) δ9.37 (s, 1H), 9.15 (d, J=8.7 Hz, 1H), 8.80 (s, 1H), 8.14-8.04 (m, 1H),7.39-7.26 (m, 3H), 7.25-7.05 (m, 4H), 6.88 (dd, J=7.6, 1.6 Hz, 1H), 6.76(s, 2H), 4.17 (s, 2H), 3.02 (p, J=6.8 Hz, 1H), 1.15 (d, J=6.9 Hz, 6H).

Example C-351-(2-isopropylphenyl)-2-methyl-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]indazol-6-yl]methyleneamino]isothiourea(C-35)

To a stirred solution of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]indazol-6-yl]methyleneamino]thiourea(0.2 g) in ACN (3 mL) and THE (3 mL) mixture were added Sodium acetate(0.090 g) and Methyl iodide (0.044 mL) at room temperature then themixture was stirred for 12 h. After completion of the reaction excesssolvent was distilled out and the crude was dissolved in Ethyl acetate.The organic layers were washed with water and brine solution then driedover Sodium sulfate and concentrated under reduced pressure to get thecrude product. The crude product was purified by column chromatographyusing Ethyl acetate and Heptane as eluent to get the title compound(0.09 g).

HPLC/MS (method 1): Rt=4.893 min; m/z=568.4 (M+1)⁺; ¹H NMR (300 MHz,DMSO-d6) δ 9.09 (s, 1H), 8.51 (s, 1H), 8.30 (d, J=8.3 Hz, 1H), 8.19 (d,J=5.1 Hz, 1H), 8.13-7.79 (m, 2H), 7.48-7.13 (m, 9H), 7.05 (d, J=8.3 Hz,3H), 6.32 (s, 3H), 4.13 (d, J=14.4 Hz, 5H), 3.30-3.19 (m, 1H), 2.36 (s,3H), 1.19 (t, J=7.4 Hz, 10H).

Example C-366-[(E)-[(Z)-[3-(2-isopropylphenyl)thiazolidin-2-ylidene]hydrazono]methyl]-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine (C-36)

To a stirred solution of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]carbamimidoyl]indazol-6-yl]methyleneamino]thiourea(0.2 g) in Acetone (5 mL) were added Potassium carbonate (0.250 g) and1-Bromo-2-chloro ethane (0.130 g) at room temperature and the wholereaction mixture was heated at 70° C. for 12 h. After completion of thereaction, the reaction mixture was diluted with Ethyl acetate thenwashed with water and brine solution. The organic layers were dried overSodium sulfate and concentrated under reduced pressure to get the crudeproduct. The crude product was purified by column chromatography usingEthyl acetate and Heptane as eluent to get the title compound (0.140 g).HPLC/MS (method 1): Rt=5.028 min; m/z=580.1 (M+1)⁺; ¹H NMR (300 MHz,DMSO-d6) δ 8.30 (d, J=8.5 Hz, 1H), 8.24 (s, 1H), 7.81 (s, 1H), 7.67 (d,J=8.6 Hz, 1H), 7.53-7.40 (m, 1H), 7.40-7.23 (m, 5H), 7.05 (d, J=8.4 Hz,2H), 6.31 (s, 2H), 4.11 (s, 4H), 3.90 (dt, J=9.9, 5.7 Hz, 1H), 3.37 (d,J=7.1 Hz, 5H), 3.03 (p, J=6.9 Hz, 1H), 1.19 (t, J=6.7 Hz, 6H).

Example C-376-[(E)-[(Z)-[3-(2-isopropylphenyl)-1,3-thiazinan-2-ylidene]hydrazono]methyl]-1-methyl-N-[4-(trifluoromethoxy)phenyl]indazole-3-carboxamidine(C-37)

To a stirred solution of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[N-[4-(trifluoromethoxy)phenyl]Carbamimidoyl]indazol-6-yl]methyleneamino]thiourea(0.2 g) in 2-Butanone (5 mL) were added Potassium carbonate (0.125 g)and 1-Bromo-2-chloro ethane (0.068 g) at room temperature then themixture was heated at 100° C. for 4 h. After completion of the reaction,the reaction mixture was diluted with Ethyl acetate then washed withwater and brine solution. The organic layers were dried over Sodiumsulfate and concentrated under reduced pressure to get the crudeproduct. The crude product was purified by column chromatography usingEthyl acetate and Heptane as eluent to get the title compound (0.140 g).HPLC/MS (method 1): Rt=4.704 min; m/z=594.1 (M+1)⁺; ¹H NMR (300 MHz,DMSO-d6) δ 8.26 (d, J=8.5 Hz, 1H), 8.04 (s, 1H), 7.77 (s, 1H), 7.64 (d,J=8.4 Hz, 1H), 7.44-7.18 (m, 6H), 7.04 (d, J=8.3 Hz, 2H), 6.29 (s, 2H),4.08 (s, 3H), 3.72 (s, 1H), 3.51-3.39 (m, 1H), 3.19-2.84 (m, 3H), 2.24(s, 2H), 1.29-1.11 (m, 8H).

Example C-381-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[[4-(trifluoromethoxy)benzenecarboximidoyl]amino]indazol-6-yl]methyleneamino]thiourea (C-38) Step 1:N-(6-bromo-1-methyl-indazol-3-yl)-4-(trifluoromethoxy)benzamidine

A suspension of methyl 4-(trifluoromethoxy)benzenecarboximidothioatehydroiodide (1.48 g), 6-bromo-1-methyl-indazol-3-amine (0.92 g) andPyridine (0.82 mL) in THE (10 mL) was heated at 80° C. for 16 h. Thereaction mixture was concentrated to dryness (2.3 g) and the crudeproduct was used without further purification.

Step 2:N-[1-methyl-6-[(E)-prop-1-enyl]indazol-3-yl]-4-(trifluoromethoxy)benzamidine

A solution ofN-(6-bromo-1-methyl-indazol-3-yl)-4-(trifluoromethoxy)benzamidine (2.3g), [(E)prop-1-enyl]boronic acid (0.72 g),[1,1′-Bis(diphenylphosphino)ferrocene]dichloropaladium(I) (0.203 g) andPotassium Carbonate (1.5 g) in DME/H₂O (20:1, 20 mL) was heated atreflux for 16 h. The reaction mixture was concentrated to dryness thendiluted with DCM and washed with brine solution, dried over MagnesiumSulfate, filtered and concentrated. Purification of the crude reactionmixture by silica gel chromatography using a gradient ofEtOAc/cyclohexane afforded the title compound (534 mg). HPLC/MS (method2): Rt=0.95 min; m/z=413 (M+).

Step 3:N-(6-formyl-1-methyl-indazol-3-yl)-4-(trifluoromethoxy)benzamidine

To a stirred solution ofN-[1-methyl-6-[(E)-prop-1-enyl]indazol-3-yl]-4-(trifluoromethoxy)benzamidine(0.534 g) in THF/H₂O (1:1, 20 mL) was added Osmium tetroxide (2.5%solution in t-BuOH, 0.29 mL) then NalO4 (0.610 g). The reaction mixturewas then stirred for 16 h and quenched with aqueous Sodium Sulfite (100mL) and extracted with EtOAc. The organic phase was separated, driedover Magnesium Sulfate, filtered, concentrated to dryness (0.557 g) andused without further purification.

Step 4:1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[[4-(trifluoromethoxy)benzenecarboximidoyl]amino]indazol-6-yl]methyleneamino]thiourea

A stirred solution ofN-(6-formyl-1-methyl-indazol-3-yl)-4-(trifluoromethoxy)benzamidine(0.557 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.386 g) in EtOH (6mL) was heated at 70° C. for 2 h. The resultant precipitate was isolatedby filtration, washed with cold EtOH to afford the title compound (0.405g). HPLC/MS (method 2): Rt=1.08 min; m/z=554 (M+1)+.

Example C-39N-[6-[(E)-[(Z)-[3-(2-isopropylphenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]-1-methyl-indazol-3-yl]-4-(trifluoromethoxy)benzamidine(C-39)

A stirred solution of1-(2-isopropylphenyl)-3-[(E)-[1-methyl-3-[[4-(trifluoromethoxy)benzenecarboximidoyl]amino]indazol-6-yl]methyleneamino]thiourea (0.283g), Methyl bromoacetate (0.16 g) and Sodium Acetate (0.17 g) in EtOH (5mL) was heated at 50° C. for 16 h. The reaction mixture was concentratedto dryness and the resultant crude oil was purified by tituration withAcetonitrile to afford the title compound (0.313 g). HPLC/MS (method 1):RT=1.08 min; m/z=594 (M+1)⁺. 1H NMR (400 MHz, THF-d8) δ 8.34 (s, 1H),8.27-8.18 (m, 2H), 7.93 (d, J=8.6 Hz, 1H), 7.66-7.59 (m, 2H), 7.43 (ddd,J=17.9, 7.6, 1.5 Hz, 2H), 7.39-7.31 (m, 2H), 7.26 (td, J=7.5, 1.6 Hz,1H), 7.15 (dd, J=7.8, 1.4 Hz, 1H), 4.10-3.94 (m, 5H), 3.57 (dq, J=2.2,1.1 Hz, 9H), 2.87 (h, J=6.8 Hz, 1H), 2.49 (s, 5H), 1.72 (dtt, J=3.1,2.1, 1.0 Hz, 12H), 1.20 (dd, J=10.3, 6.8 Hz, 6H).

Examples listed in Table C were prepared by the procedure analogous toabove example as or by derivatization thereof.

TABLE C               No               Ar—Q

              R¹             HPLC/ MS             Rt min C-1

554.2  (method 1) 1.76 C-2

594.3  (method 1) 1.73 C-3

582.3  (method 1) 1.72 C-4

613   (method 2) 1.29 C-5

584   (method 1) 2.24 C-6

624   (method 1) 2.29 C-7

570   (method 1) 2.02 C-8

610   (method 1) 2.05 C-9

582   (method 1) 1.48 C-10

610   (method 1) 1.61 C-11

598   (method 1) 2.28 C-12

638   (method 1) 2.33 C-13

584   (method 1) 2.24 C-14

624   (method 1) 2.23 C-15

568.35 (method 1) 1.66 C-16

608.1  (method 1) 1.66 C-17

578   (method 1) 2.04 C-18

616.9  (method 1) 2.05 C-19

594.3  (method 1) 1.88 C-20

557   (method 1) 2.24 C-21

597   (method 1) 2.29 C-22

580.1  (method 1) 1.68 C-23

622.3  (method 1) 1.73 C-24

537   (method 1) 2.34 C-25

579.1  (method 1) 2.35 C-26

555   (method 1) 1.84 C-27

595   (method 1) 1.91 C-28

596.8  (method 1) 2.36 C-29

603.9  (method 1) 2.02 C-30

641.95 (method 1) 2.08 C-31

538   (method 1) 2.03 C-32

578   (method 1) 2.02 C-33

539   (method 1) 2.11 C-34

579   (method 1) 1.91 C-35

568.4  (method 1) 1.95 C-36

580.1  (method 1) 2.03 C-37

594.1  (method 1) 1.94 C-38

554   (method 2) 1.08 C-39

594   (method 2) 1.08 C-40

582   (method 1) 2.13 C-41

622   (method 1) 2.16 C-42

568   (method 1) 1.78 C-43

608   (method 1) 1.76 C-44

608   (method 1) 1.89 C-45

539.95 (method 1) 1.62 C-46

580   (method 1) 1.67 C-47

632.3  (method 1) 1.53 C-48

660.4  (method 1) 1.65 C-49

566.1  (method 1) 1.71 C-50

566.3  (method 1) 1.57

BIOLOGICAL EXAMPLES Example B1: Action on Yellow Fever Mosquito (Aedesaegypti)

For evaluating control of yellow fever mosquito (Aedes aegypti) the testunit consisted of 96-well-microtiter plates containing 200 μl of tapwater per well and 5-15 freshly hatched A. aegypti larvae.

The active compounds or mixtures were formulated using a solutioncontaining 75% (v/v) water and 25% (v/v) DMSO. Different concentrationsof formulated compounds or mixtures were sprayed onto the insect diet at2.5 μl, using a custom built micro atomizer, at two replications. Forexperimental mixtures in these tests identical volumes of both mixingpartners at the desired concentrations respectively, were mixedtogether.

After application, microtiter plates were incubated at 28±1° C., 80±5%RH for 2 days. Larval mortality was then visually assessed.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9,C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21,C-22, C-23, C-24, C-26, C-27, C-28, C-31, C32, C-33, C-34, C-35, C-36,C-37, C-38, C-39, C-45 and C-46 at 800 ppm showed at least 50% mortalityin comparison with untreated controls.

Example B2: Action on Orchid Thrips (Dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay were obtained from acolony maintained continuously under laboratory conditions. For testingpurposes, the test compound is diluted in a 1:1 mixture of acetone:water(vol:vol), plus Kinetic® HV at a rate of 0.01% v/v.

Thrips potency of each compound was evaluated by using afloral-immersion technique. All petals of individual, intact orchidflowers were dipped into treatment solution and allowed to dry in Petridishes. Treated petals were placed into individual re-sealable plasticalong with about 20 adult thrips. All test arenas were held undercontinuous light and a temperature of about 28° C. for duration of theassay. After 3 days, the numbers of live thrips were counted on eachpetal. The percent mortality was recorded 72 hours after treatment.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-11, C-15, C-19,C-20, C-21, C-22, C23, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33,C-34, C-35, C-36, C-37, C-38, C-39, C-42, C-43, C-44 and C-46 at 500 ppmshowed at least 75% mortality in comparison with untreated controls.

Example B3: Action on Boll Weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unitconsisted of 96-well-microtiter plates containing an insect diet and5-10 A. grandis eggs.

The compounds were formulated using a solution containing 75% (v/v)water and 25% (v/v) DMSO. Different concentrations of formulatedcompounds were sprayed onto the insect diet at 5 μl, using a custombuilt micro atomizer, at two replications.

After application, microtiter plates were incubated at about 25+1° C.and about 75+5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9,C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21,C-22, C-23, C-26, C-27, C-28, C-31, C-32, C33, C-34, C-35, C-36, C-37,C-38, C-39, C-45 and C-46 at 800 ppm showed at least 75% mortality incomparison with untreated controls.

Example B4: Action on Silverleaf Whitefly (Bemisia argentifoli) (Adults)

The active compounds were formulated by a Tecan liquid handler in 100%cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppmsolution was serially diluted in 100% cyclohexanone to make interimsolutions. These served as stock solutions for which final dilutionswere made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10 mlglass vials. A nonionic surfactant (Kinetic®) was included in thesolution at a volume of 0.01% (v/v). The vials were then inserted intoan automated electrostatic sprayer equipped with an atomizing nozzle forapplication to plants/insects.

Cotton plants at the cotyledon stage (one plant per pot) were sprayed byan automated electrostatic plant sprayer equipped with an atomizingspray nozzle. The plants were dried in the sprayer fume hood and thenremoved from the sprayer. Each pot was placed into a plastic cup andabout 10 to 12 whitefly adults (approximately 3-5 days old) wereintroduced. The insects were collected using an aspirator and a nontoxicTygon® tubing connected to a barrier pipette tip. The tip, containingthe collected insects, was then gently inserted into the soil containingthe treated plant, allowing insects to crawl out of the tip to reach thefoliage for feeding. Cups were covered with a reusable screened lid.Test plants were maintained in a growth room at about 25° C. and about20-40% relative humidity for 3 days, avoiding direct exposure tofluorescent light (24 hour photoperiod) to prevent trapping of heatinside the cup. Mortality was assessed 3 days after treatment, comparedto untreated control plants.

In this test, compounds C-1, C-2, C-4, C-22, C-23, C-28, C-30, C-31,C-32, C-33, C-35, C-38, C-39 and C-44 at 300 ppm showed at least 75%mortality in comparison with untreated controls.

Example B5: Action on Tobacco Budworm (Heliothis virescens)

For evaluating control of tobacco budworm (Heliothis virescens) the testunit consisted of 96-well-microtiter plates containing an insect dietand 15-25 H. virescens eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 10 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 28+1° C.and about 80+5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-11,C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-20, C-21, C-22, C-23,C-24, C-25, C-26, C-27, C-28, C-31, C-32, C33, C-34, C-35, C-36, C-37,C-38, C-39, C-45 and C-46 at 800 ppm showed at least 75% mortality incomparison with untreated controls.

Example B6: Action on Diamond Back Moth (Plutella xylostella)

The active compound is dissolved at the desired concentration in amixture of 1:1 (v/v) distilled water:acetone. Surfactant (Kinetic® HV)is added at a rate of 0.01% (v/v). The test solution is prepared at theday of use.

Leaves of cabbage were dipped in test solution and air-dried. Treatedleaves were placed in petri dishes lined with moist filter paper andinoculated with ten 3rd instar larvae. Mortality was recorded 72 hoursafter treatment. Feeding damages were also recorded using a scale of0-100%.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-10,C-11, C-12, C-13, C-14, C-15, C-17, C-18, C-19, C-20, C-21, C-22, C-23,C-24, C-25, C-26, C-27, C-28, C-29, C-30, C31, C-32, C-33, C-34, C-35,C-36, C-37, C-38, C-39, C-42, C-43, C-44, C-45 and C-46 at 500 ppmshowed at least 75% mortality in comparison with untreated controls.

Example B7: Action on Southern Armyworm (Spodoptera eridania), 2ndInstar Larvae

The active compounds were formulated by a Tecan liquid handler in 100%cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppmsolution was serially diluted in 100% cyclohexanone to make interimsolutions. These served as stock solutions for which final dilutionswere made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20 mlglass vials. A nonionic surfactant (Kinetic®) was included in thesolution at a volume of 0.01% (v/v). The vials were then inserted intoan automated electrostatic sprayer equipped with an atomizing nozzle forapplication to plants/insects.

Lima bean plants (variety Sieva) were grown 2 plants to a pot andselected for treatment at the 1st true leaf stage. Test solutions weresprayed onto the foliage by an automated electrostatic plant sprayerequipped with an atomizing spray nozzle. The plants were dried in thesprayer fume hood and then removed from the sprayer. Each pot was placedinto perforated plastic bags with a zip closure. About 10 to 11 armywormlarvae were placed into the bag and the bags zipped closed. Test plantswere maintained in a growth room at about 25° C. and about 20-40%relative humidity for 4 days, avoiding direct exposure to fluorescentlight (24 hour photoperiod) to prevent trapping of heat inside the bags.Mortality and reduced feeding were assessed 4 days after treatment,compared to untreated control plants.

In this test, compounds C-1, C-2, C-5, C-6, C-7, C-8, C-10, C-11, C-12,C-13, C-14, C-15, C16, C-17, C-18, C-19, C-21, C-22, C-23, C-26, C-27,C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-38, C-39, C-44 andC-45 at 300 ppm showed at least 75% mortality in comparison withuntreated controls.

We claim:
 1. A compound of formula I

wherein A¹ is N or CR^(A); A² is N or CR^(B); A³ is N or CR^(B1); W isO, S(═O)_(m), or NR⁶; R^(A), R^(B) and R^(B1) independently of eachother are H, halogen, N₃, OH, CN, NO₂, —SCN, —SF₅, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl,alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted orsubstituted with halogen, C(═O)—OR^(a), NR^(b)R^(c),C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy,phenylcarbonyl, phenylthio, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f); Q is —N═C(X)—, —N(R²)—C(═NR)—,or —N(R²)—C(═S)—; wherein Ar is bound to either side of Q; X isidentical or different, H, halogen, SR⁷, OR⁸, N(R³)₂, —CR⁴═N(OCH₃), CN,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, wherein thealkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted orsubstituted with halogen; phenyl, or —CH₂-phenyl, wherein the phenylrings are unsubstituted or substituted with R⁵; R⁵ is halogen, N₃, OH,CN, NO₂, —SCN, —SF, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C1-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,C₃-C₆-cycloalkylthio, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkylthio,alkenyl, alkynyl, cycloalkyl, cycloalkoxy and cycloalkylthio moietiesare unsubstituted or substituted with halogen, C(O)—OR^(a), NR^(b)R^(c),C₁-C₆-alkylen-NR^(b)R^(c), O—C₁-C₆-alkylen-NR^(b)R^(c),C₁-C₆-alkylen-CN, NH—C₁-C₆-alkylen-NR^(b)R^(c), C(O)—NR^(b)R^(c),C(O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e); R² is H, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted orsubstituted with halogen, C(O)—OR^(a), C₁-C₆-alkylen-NR^(b)R^(c),C₁-C₆-alkylen-CN, C(O)—NR^(b)R^(c), C(O)—R^(d), SO₂NR^(b)R^(c),S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f); R is identical or different, H,CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, whereinthe alkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted orsubstituted with halogen, SR⁷, OR⁸, N(R³)₂, phenyl, or —CH₂-phenyl,wherein the phenyl rings are unsubstituted or substituted with R⁵; R⁴ isH, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, C(═O)—OR^(a),C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c),C(═O)—R^(d), phenyl, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f); R⁷ is C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted orsubstituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl, or—CH₂-phenyl, wherein the phenyl rings are unsubstituted or substitutedwith R^(f); R⁸ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, C(═O)—OR^(a),C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c),C(═O)—R^(d), SO₂NR^(b)R^(c), phenyl, or —CH₂-phenyl, wherein the phenylrings are unsubstituted or substituted with R^(f); R³, R⁶ are, identicalor different, H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, C(═O)—OR^(a),C₁-C₆-alkylene-NR^(b)R^(c), C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c),C(═O)—R^(d), SO₂NR^(b)R^(c), S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl,wherein the phenyl rings are unsubstituted or substituted with R^(f); Aris phenyl or 5- or 6-membered hetaryl, which are unsubstituted orsubstituted with R^(Ar), wherein R^(Ar) is halogen, N₃, OH, CN, NO₂,—SCN, —SF, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c),C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e), phenyl, phenoxy,phenylcarbonyl, phenylthio or —CH₂-phenyl, wherein phenyl rings areunsubstituted or substituted with R^(f); R¹ is a moiety of formulaY—Z-T-R¹¹ or Y—Z-T-R¹²; wherein Y is —CR^(ya)═N—, wherein the N is boundto Z; NR^(yc)—C(═O)—, wherein C(═O) is bound to Z; or —NR^(yc)—C(═S)—,wherein C(═S) is bound to Z; Z is a single bond; —NR^(zc)—C(═O)—,wherein C(═O) is bound to T; —NR^(zc)—C(═S)—, wherein C(═S) is bound toT; —N═C(S—R^(za))—, wherein T is bound to the carbon atom; or—NR^(zc)—C(S—R^(za))═, wherein T is bound to the carbon atom; T is O, Nor N—R^(T); R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), aryl, arylcarbonyl,aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl, hetaryl, carbonyl-hetaryl,hetaryl-C₁-C₄-alkyl or hetaryloxy-C₁-C₄-alkyl, wherein the phenyl ringsare unsubstituted or substituted with R^(g) and wherein the hetaryl is a5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclichetaryl; R¹² is a radical of the formula A¹;

wherein # indicates the point of attachment to T; R¹²¹, R¹²², R¹²³ are,identical or different, H, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,C₂-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonlyoxy,C₁-C₆-alkenylcarbonlyoxy, C₃-C₆-cycloalkylcarbonlyoxy, wherein thealkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and cycloalkylmoieties are unsubstituted or substituted with halogen, or NR^(b)R^(c),or one of R¹²¹, R¹²², R¹²³ may also be oxo; R¹²⁴ is H, C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy, or C₂-C₆-alkenyloxy, wherein thealkyl, alkoxy, alkenyl and alkenyloxy moieties are unsubstituted orsubstituted with halogen; and where R^(ya) is H, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl,C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl,alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted orsubstituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c),S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f); R^(yc), R^(zc) are, identicalor different, H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₄-alkyl-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₁-C₄-alkyl-C₃-C₆-cycloalkyl, or C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, whereinthe alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moietiesare unsubstituted or substituted with halogen; R^(T) is H, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkyl-C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted orsubstituted with halogen, C(═O)—OR^(a), C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), SO₂NR^(b)R^(c),S(═O)_(m)R^(e), phenyl, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f); R^(zc) together with R^(T) ifpresent, may form C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group,where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2CH₂ moieties may be replaced by O or S and/or wherein the linearC₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted orsubstituted with R^(h); R^(za) is H, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₂-C₆-alkenyl, tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl,C₁-C₄-alkyl-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₁-C₄-alkyl-C₃-C₆-cycloalkoxy, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, C(═O)—NR^(b)R^(c), C(═O)—R^(d), phenyl,phenylcarbonyl, or —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f); R^(za) together with R^(T) ifpresent, may form C₁-C₆-alkylene or a linear C₂-C₆-alkenylene group,where in the linear C₁-C₆-alkylene and the linear C₂-C₆-alkenylene a CH₂moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2CH₂ moieties may be replaced by O or S and/or wherein the linearC₁-C₆-alkylene and the linear C₂-C₆-alkenylene may be unsubstituted orsubstituted with R^(h); R^(a), R^(b) and R are, identical or different,H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein the alkyl, alkoxy, alkenyl,alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted orsubstituted with halogen, C₁-C₆-alkylene-CN, phenyl, or —CH₂-phenyl,wherein the phenyl rings are unsubstituted or substituted with R^(f);R^(d) is H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, phenyl, or —CH₂-phenyl,wherein the phenyl rings are unsubstituted or substituted with R^(f);R^(e) is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,wherein the alkyl, cycloalkyl moieties are unsubstituted or substitutedwith halogen, phenyl and —CH₂-phenyl, wherein the phenyl rings areunsubstituted or substituted with R^(f); R^(f) is halogen, N₃, OH, CN,NO₂, —SCN, —SF, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxyx-C₁-C₄-alkyl, whereinthe alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moietiesare unsubstituted or substituted with halogen, C(═O)—OR^(a),NR^(b)R^(c), C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e); R^(g) is halogen, N₃,OH, CN, NO₂, —SCN, —SF, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl,tri-C₁-C₆-alkylsilyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, wherein thealkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties areunsubstituted or substituted with halogen, C(═O)—OR^(a), NR^(b)R^(c),C₁-C₆-alkylene-NR^(b)R^(c), O—C₁-C₆-alkylene-NR^(b)R^(c),C₁-C₆-alkylene-CN, NH—C₁-C₆-alkylene-NR^(b)R^(c), C(═O)—NR^(b)R^(c),C(═O)—R^(d), SO₂NR^(b)R^(c), or S(═O)_(m)R^(e); R^(h) is halogen, OH,C₁-C₆-alkyl, C₃-C₆-cycloalkyl, or CN; m is 0, 1, or 2; with a provisothat when Z is a single bond, R^(T) is other than H; or an N-oxide,stereoisomers, tautomer, or agriculturally or veterinarily acceptablesalts thereof.
 2. The compound of formula I according to claim 1,wherein W is O, A¹ is CR^(A), A² is CR^(B), and A³ is N.
 3. The compoundof formula I according to claim 1, wherein W is N, A¹ is CR^(A), A² isCR^(B), and A³ is N.
 4. The compound of formula I according to claim 1,wherein W is O, A¹ is CR^(A), A² is CR^(B), and A³ is CR^(B1).
 5. Thecompound of formula I according to claim 1, wherein W is N, A¹ isCR^(A), A² is CR^(B), and A³ is CR^(B1).
 6. The compound of formula Iaccording to claim 1, wherein W is N, A¹ is N, A² is N, and A³ isCR^(B1).
 7. The compound of formula I according to claim 1, wherein W isS(═O)_(m), A¹ is CR^(A), A² is CR^(B), and A³ is CR^(B1).
 8. Thecompound of formula I according to claim 1, wherein R¹ is selected fromformulas YZT-1 to YZT-8, wherein

denotes attachment to the 9 membered hetaryl;

wherein R¹¹, R¹², R^(T), R^(ya), R^(za) and R^(zc) are as defined inclaim
 1. 9. The compound of formula I according to claim 1, wherein Aris selected from formulas Ar-1 to Ar-12.


10. A composition comprising one compound of formula I according toclaim 1, an N-oxide or an agriculturally acceptable salt thereof, and afurther active substance.
 11. A method for combating or controllinginvertebrate pests, comprising contacting said pest or its food supply,habitat or breeding grounds with a pesticidally effective amount of atleast one compound according to claim
 1. 12. A method for protectinggrowing plants from attack or infestation by invertebrate pests,comprising contacting a plant, or soil or water wherein the plant isgrowing, with a pesticidally effective amount of at least one compoundaccording to claim
 1. 13. Seed comprising a compound according to claim1, or a stereoisomer or agriculturally acceptable salt thereof, in anamount of from 0.1 g to 10 kg per 100 kg of seed.
 14. A compound of theformula I according to claim 1, or an agriculturally acceptable saltthereof, for use in protecting growing plants from attack or infestationby invertebrate pests.
 15. A method for treating or protecting an animalfrom infestation or infection by invertebrate pests comprising bringingthe animal in contact with a pesticidally effective amount of at leastone compound of the formula I according to claim 1, a stereoisomerthereof and/or at least one veterinarily acceptable salt thereof.